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[ CAS No. 4389-45-1 ] {[proInfo.proName]}

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Chemical Structure| 4389-45-1
Chemical Structure| 4389-45-1
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Product Details of [ 4389-45-1 ]

CAS No. :4389-45-1 MDL No. :MFCD00007745
Formula : C8H9NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :WNAJXPYVTFYEST-UHFFFAOYSA-N
M.W : 151.16 Pubchem ID :78101
Synonyms :

Calculated chemistry of [ 4389-45-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.12
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.77
TPSA : 63.32 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.43 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.86
Log Po/w (XLOGP3) : 2.53
Log Po/w (WLOGP) : 1.28
Log Po/w (MLOGP) : 0.21
Log Po/w (SILICOS-IT) : 0.95
Consensus Log Po/w : 1.17

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -2.71
Solubility : 0.296 mg/ml ; 0.00196 mol/l
Class : Soluble
Log S (Ali) : -3.51
Solubility : 0.0471 mg/ml ; 0.000312 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.78
Solubility : 2.5 mg/ml ; 0.0166 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.0

Safety of [ 4389-45-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 4389-45-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 4389-45-1 ]

[ 4389-45-1 ] Synthesis Path-Downstream   1~14

  • 1
  • [ 4389-45-1 ]
  • [ 57772-50-6 ]
YieldReaction ConditionsOperation in experiment
97% With lithium aluminium tetrahydride; In tetrahydrofuran; at 20℃; for 3.5h; General procedure: To a suspension of lithium aluminum hydride (20.4 mmol) in THF (10 mL) was added benzoic acid (8.5 mmol) dissolved in THF (24 mL) dropwise over 20 minutes at room temperature. The reaction continued to stir at room temperature for 3.5 h, and then was quenched at 0 C with H2O (10 mL). The suspension was filtered through a Celite plug with EtOAc (100 mL), washed with brine (30 mL), dried with MgSO4 and concentrated in vacuo.
  • 2
  • [ 4389-45-1 ]
  • [ 77287-34-4 ]
  • [ 19181-54-5 ]
YieldReaction ConditionsOperation in experiment
86% With formamidine acetic acid; at 160℃; for 16h; 2-Amino-3-methylbenzoic acid (100 g, 0.66 mol), formamidine acetate (206 g, 1 .98 mol) and formamide (26 mL, 0.6600 mol) were mixed in a 2L R.B fitted with Mechanical stirrer. The reaction mixture was heated at 160 C for 16h. The reaction completion was monitored by LCMS. After completion, the reaction mixture was cooled to was RT and diluted with 2N NaOH solution (300 mL). After stirring at the same temperature for 15min, the reaction mixture neutralised with 1.5N HCI solution. The solid precipitated was filtered off, washed with ice cold water and dried under vacuum to yield (90 g, 86% yield) of the titled compound as an off white solid. H NMR (DMSO-d6, 400MHz) delta 12.21 ( bs, 1 H), 8.10 (s, 1 H), 7.95-7.93 (dd, J = 8.8, 7.9 Hz, 1 H), 7.65-7.63 (d, J = 7.9 Hz, 1 H), 7.39-7.35 (t, J = 15.2 Hz, 1 H), 2.51 (s, 3H).
78% at 140℃; General procedure: To a three necked flask, substituted anthranilic acid (1 meq.) was added in excess of formamide (6 meq). The reaction mixture was then heated at 140 C for 4-6 h. The reaction was monitored with thin layer chromatography and upon completion; ice was added to the reaction mixture. The resultant solid was filtered, washed with water, dissolved in ethyl acetate, dried over MgSO4 and concentrated to obtain the pure desired product. Where product did not precipitate on addition of ice, the reaction mixture was extracted with ethyl acetate, dried over MgSO4 and concentrated to obtain the desired quinazolin-4(3H)-one derivatives 1-9, 11-15, 17-21 and 23-25.The amino derivatives 10, 16 and 22 were prepared using the following general procedure:To a reaction flask, substituted nitroquinazolin-4(3H)-one derivative (0.3 g, 1.56 mmol) was added followed by addition of 6 mL ethyl acetate and SnCl2·2H2O (2.12 g, 9.42 mmol), then reaction mixture was refluxed for 8 h. The reaction mixture was cooled to room temperature and quenched with saturated sodium bicarbonate solution, followed by repeated extraction with ethyl acetate (3 × 50 mL). The organic layers were combined, dried over anhydrous MgSO4 and concentrated to obtain the desired amino substituted quinazolin-4(3H)-one derivatives 10, 16 and 22.The substituted anthranilic acid (1 g) was dissolved in excess acetic anhydride (10 mL) and the resulting reaction mixture was stirred at room temperature for 4-7 h. The reaction was monitored for completion using thin layer chromatography. The solvent was evaporated under vacuum and the resultant residue was stirred with ammonia solution for 7 h. Upon completion, the reaction mixture was extracted with ethyl acetate (3 × 10 mL), the organic extracts were combined, dried over MgSO4 and evaporated to obtain compounds 26-30, 31a and 32. The 2-methyl-8-nitroquinazolin-4(3H)-one intermediate (31a) was reduced to compound 31 using the same procedure as reported in Scheme 1 for the synthesis of compounds 10, 16 and 22.
at 130 - 135℃; for 4h; General procedure: Compound 18 was prepared accordingto the procedure previously reported.39 A mixture of anthranilicacid 11 (0.1 mol) and formamide (18 g, 0.4 mol) was heated at130-135 C. After the mixture had been stirred for 4 h, water(40 mL) was added. The reaction mixture was cooled to 60 C,and water (20 mL) was added to the mixture. After the mixturehad been stirred for 30 min, the precipitated product wasfiltered off with suction. The crude products were recrystallizedwith ethanol to give compound 18 in yields of 80-95%.
  • 3
  • [ 75-44-5 ]
  • [ 4389-45-1 ]
  • [ 66176-17-8 ]
  • 4
  • [ 32315-10-9 ]
  • [ 4389-45-1 ]
  • [ 66176-17-8 ]
YieldReaction ConditionsOperation in experiment
94% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; a 8-Methyl-1H-benzo[d][1,3]oxazine-2,4-dione To a solution of 2-amino-3-methylbenzoic acid (9.07 g, 60 mmol) in THF (60 mL) was added simultaneously diisopropylethylamine (20.9 mL) and a solution of triphosgene (5.94 g, 20 mmol) in dichloromethane (60 mL) over 30 minutes period. After the addition was completed, the mixture stirred at ambient temperature for 16 hours. Solid was filtered and washed with ether (2*100 mL) and H2O (3*50 mL), and dried in high vacuum to afford the title compound (10.02 g, 94% yield) as a white solid. 1H NMR (DMSO) delta 11.02 (s, 1H), 7.76 (d, 1H, J=7.7 Hz), 7.57 (d, 1H, J=7.5 Hz), 7.17-7.13 (m, 1H), 2.32 (s, 3H).
94% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; a) 8-Methyl-1H-benzo[d][1,3]oxazine-2,4-dione To a solution of 2-amino-3-methylbenzoic acid (9.07 g, 60 mmol) in THF (60 mL) was added simultaneously diisopropylethylamine (20.9 mL) and a solution of triphosgene (5.94 g, 20 mmol) in dichloromethane (60 mL) over 30 minutes period. After the addition was completed, the mixture stirred at ambient temperature for 16 hours. Solid was filtered and washed with ether (2*100 mL) and H2O (3*50 mL), and dried in high vacuum to afford the title compound (10.02 g, 94% yield) as a white solid. 1H NMR (DMSO): delta 11.02 (s, 1H), 7.76 (d, 1H, J=7.7 Hz), 7.57 (d, 1H, J=7.5 Hz), 7.17-7.13 (m, 1H), 2.32 (s, 3H).
86.4% In tetrahydrofuran; at 20℃; for 0.25h; Example 2268-Methyl- 1 -(3 -(4-(pyrimidin-2-yl)piperazine- 1 -carbonyl)benzyl)quinazoline-2,4( lH,3H)-dione a) 8-Methyl- lH-benzo[<i][l,3]oxazine-2,4-dione: To a solution of 2-amino-3-methylbenzoic acid (5.03 g, 33.3 mmol) in THF (50 mL) was added triphosgene (9.92 g, 33.4 mmol). The mixture was stirred at room temperature for 15 min and then filtered. The precipitate was washed by THF and water, dried to give the title compound (5.10 g, 86.4% yield) as white solid. MS: m/z 178.1 [M+H]+.
86.4% In tetrahydrofuran; at 20℃; for 0.25h; To a solution of 2-amino-3-methylbenzoic acid (5.03 g, 33.3 mmol) in THF (50 mL) was added triphosgene (9.92 g, 33.4 mmol). The mixture was stirred at room temperature for 15 min and then filtered. The precipitate was washed by THF and water, dried to give the title compound (5.10 g, 86.4% yield) as white solid. MS: m/z 178.1 [M+H]+.
78% With triethylamine; In tetrahydrofuran; at 0 - 20℃; for 18h; General procedure: Toa solution of amino-benzoic acid (2.90 mmol, 1 eq) in anhydrous THF (25 mL), triethylamine (2.90 mmol, 1 eq) was added and the mixture was cooled down to 0C. Then triphosgene (0.97 mmol, 1 eq) was added portion wise and the reaction allowed to reach room temperature and left stirring for 18 hours. 1mL of H2O was carefully added to the mixture and the solvent was removed under reduced pressure. The residue was precipitated from H2O, affording pure product.
In tetrahydrofuran; at 20℃; for 4h; General procedure: To a solution of different substituted 2-aminobenzoic acid (3 mmol) in 15 mL of THF was added triphosgene (0.30 g, 1 mmol). The mixture was stirred at room temperature and monitored with TLC. After more than 4 h, the solvent was evaporated and the residue was dissolved in 15 mL of EtOH. The hydrazine hydrate (80 %) (0.94 g, 15 mmol) was added to this mixture dropwise. After 2 h, the reaction was completed, 30 mL of ethyl acetate was added. The solution was washed with 1 mol/L hydrochloric acid solution, saturated sodium bicarbonate solution, and brine. The ethyl acetate solution was dried and evaporated, and the residue was applied to a flash column chromatography by eluting with ethyl acetate to give the compounds 1a-f.
General procedure: Compound 12 was prepared according tothe procedure previously reported.36 A mixture of anthranilicacid 11 (50 mmol) and tetrahydrofuran (THF, 100 mL) wasstirred at -10 C for 30 min. Then, a solution of triphosgene(BTC, 50 mmol) in THF (30 mL) was added dropwise to themixture described above. After that, the mixture was stirred for1 h at -10 C, followed by 18-24 h at 20-25 C. The solventwas removed under reduced pressure, and anhydrous ether(150 mL) was added to the obtained residue while the mixturewas being vigorously stirred. The precipitate was collected byfiltration, washed with anhydrous ether, and dried to givecompound 12 in yields of 80-90%.
In tetrahydrofuran; at 20℃; (4) Add 5g of raw material 4 and tetrahydrofuran to a 100ml three-necked flask and stir at room temperature, and add 8.65g of triphosgene in portions.The reaction was followed by TLC until the raw materials disappeared, dissolved, and the solid was washed with n-hexane solution multiple times to obtain intermediate 5.

  • 5
  • [ 4389-45-1 ]
  • [ 181765-85-5 ]
  • [ 206531-05-7 ]
  • 6
  • [ 7664-93-9 ]
  • [ 4389-45-1 ]
  • [ 57772-50-6 ]
  • 8
  • [ 4389-45-1 ]
  • [ 66176-17-8 ]
YieldReaction ConditionsOperation in experiment
94% With bis(trichloromethyl) carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 20℃; for 16.5h; To a solution of 2-amino-3-methylbenzoic acid (9.07 g, 60 mmol) in THF (60 mL) was added simultaneously diisopropylethylamine (20.9 mL) and a solution of triphosgene (5.94 g, 20 mmol) in dichloromethane (60 mL) over 30 minutes period. After the addition was completed, the mixture stirred at ambient temperature for 16 hours. Solid was filtered and washed with ether (2 x 100 mL) and HA0 (3 x 50 m L), and dried in high vacuum to afford the title compound (10.02 g, 94 % yield) as a white SOLID. 1H NMR (DMSO) delta 11.02 (s, 1H), 7.76 (d, 1H, J=7. 7 Hz), 7.57 (d, 1H, J=7. 5 Hz), 7.17-7. 13 (m, 1H), 2.32 (s, 3H).
  • 9
  • [ 4389-45-1 ]
  • [ 4124-31-6 ]
  • [ 66176-17-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at -10 - 25℃; for 19h; A pre-dried glass lined reactor was charged with triphosgene (1 wt. , 1 eq. ) and anhydrous THF (2 vol. ) and was cooled to an internal temperature of -10 C. A second pre- dried glass lined was charged with ER-807244 (1.27 wt. , 2.5 eq. ) and anhydrous THF (3 vol.) then cooled to an internal temperature of -10 C. The contents of the first reactor were transferred into the second reactor at a rate such that internal temperature did not exceed 15 C. After complete addition, the reaction was stirred at an internal temperature of 0C for 1 hour and then gradually warmed to 25C. A sparge of nitrogen was used for 18 hours to scrub away excess phosgene with trapping of the off-gases through a 2 N NaOH solution. MTBE (3 vol. ) was added and the solvent removed by distillation under N2 purge at 40 to 46C, adding more MTBE as needed. Upon complete removal of the phosgene, the mixture was cooled to an internal temperature of 5 to 10C and the solution filtered with MTBE (3 vol. ) washes to yield ER-807245 (1.12 wt. , 0.97 eq. ) as a white crystalline solid.
  • 10
  • [ 4389-45-1 ]
  • [ 19181-54-5 ]
YieldReaction ConditionsOperation in experiment
With formamide; Step A Preparation of 8-methylquinazolin-4(3H)-one 2-Amino-3-methylbenzoic acid (1.00 g, 0.0066 mol) and formamide (12 mL) were heated together at 130 C. for 20 hr. under nitrogen. After cooling to room temperature, the solid was filtered off, washed with diethyl ether and dried in vacuo to leave 8-methylquinazolin-4(3H)-one (1.19 g). 1 H-NMR 400 MHz (CD3 OD): delta 8.06 (m, 2H), 7.68 (d, 1H), 7.41 (t, 1H), 2.59 (s, 3H); EI-MS 160 (M+).
  • 11
  • [ 4389-45-1 ]
  • [ 1885-32-1 ]
YieldReaction ConditionsOperation in experiment
98% 2-Amino-3-methylbenzoic acid (2.93 g, 19.8 mmol) in dry DMF (78 mL) was treated with 1,1-carbonyl-diimidazole (3.14 g, 19.4 mmol) at 70C under Ar for lh, after which aq. NH3 (35%, 49 mL) was added dropwise and the mixture was stirred for 16 h. The mixture was allowed to cool to 20C and was diluted with EtOAc (100 mL). The mixture was washed with water (2 x 40 mL) and brine (2 x 40 mL). The organic solution was dried and the solvent was evaporated to give (8) (2.14 g, 98%) as a white solid: mp 150-152C (lit.24 mp 150-152C); NMR ((CD3)2SO) delta 2.05 (3 H, s,), 6.35 (2 H, br), 6.41 (1 H, brt, / = 7.6 Hz,), 7.00 (1 H, brs), 7.04 (1 H, d, / = 6.8 Hz), 7.34 (1 H, dd, / = 8.0, 0.8 Hz), 7.67 (1 H, brs); 13CNMR ((CD3)2SO) delta 17.56, 113.59, 114.17, 122.99, 126.61, 132.67, 148.21, 171.73.
87% With ammonium chloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 60h;Inert atmosphere; Step A: To 2-amino-3-methylbenzoic acid (1.5 g, 10 mmol) in DMF (5 mL) at rt were added hydroxybenzatriazole (2.0 g, 13 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide (2.3 g, 12 mmol), ammonium chloride (2.3 g, 42 mmol), and diisopropylethylamine (7.5 ml, 42 mmol). The mixture was purged with N2 and stirred for 60 h. The mixture was poured into water and extracte with EtOAc (50 mL×3), and the combined extracts were washed with brine (20 mL×2), dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was dissolved in DCM and purified by silica gel chromatography eluting with 1:1 EtOAc/hexanes to afford 2-amino-3-methyl-benzamide as a white solid (1.3 g, 87%).
64% 1161) A 500 mL round bottom flask was charged with 2-amino-3-methylbenzoic acid (Combi-Blocks, 4.0 g, 26.5 mmol, 1 eq), NH4Cl (4.25 g, 79.4 mmol, 3 eq) and a stir bar. The flask was evacuated and back-filled with Ar (×3). Anhydrous DCM (100 mL) and anhydrous DMF (20 mL) were added. The resulting stirred mixture was cooled to 0 C. 1-hydroxybenzotriazole hydrate (3.93 g, 29.1 mmol, 1.1 eq) was added followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.56 g, 29.1 mmol, 1.1 eq) 5 min later. After 1 h DIPEA (32 mL, 23.9 g, 185 mmol, 7 eq) was added dropwise. The reaction was stirred at 0 C. to room temperature overnight. The volatiles were removed via rotary evaporation. The residue was diluted with water and adjusted to pH?8-9 with conc. NH3(aq). The resulting mixture was extracted with EtOAc (×3). The combined organics were dried over Na2SO4. The solids were filtered off, and the volatiles were removed via rotary evaporation. The residue was diluted with DCM and the resulting mixture was diluted with hexanes. The solids were collected via vacuum filtration. The filter cake was triturated with 10% DCM in hexanes and dried. 2.56 g (17.0 mmol, 64% yield) of 135 was collected as an off-white solid. Mass spectrum (ESI+): m/z=151 [M+1]observed.
63% With ammonia; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; at 20℃; for 16h; 00373] Step A: To solution of 2-amino-3-methylbenzoic acid (4.0 g, 26.5 mmol) in degassed DMF (40 mL) were added HOBt (4.28 g, 31.7 mmol), DIEA (5.52 mL, 31.7 mmol), and 2N NH3/MeOH (19 mL, 37.1 mmol). The solution was stirred at rt for 16 h, then. the mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 10-60% EtOAc/hexanes to afford 2-amino-3-methylbenzamide as a solid (2.52 g, 63%). 1H NMR (300 MHz, DMSO-J6) delta 2.07 (s, 3H), 6.40 - 6.47 (m, 3H), 7.06 (m, 2H), 7.42 (d, IH), 7.72 (br d, IH).
60% With ammonia; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; N,N-dimethyl-formamide; at 20℃; for 24h;Inert atmosphere; Accordingtoaliteratureprocedure,3toasolutionof2-amino-3-methylbenzoicacid(151mg,1.00mmol,1.0eq)indegassedDMF(2.00mL)wereaddedHOBt(162mg,1.20mmol,1.2eq.),EDCI.HCl(230mg,1.20mmol,1.2eq.),N,N-diisopropylethylamine(350muL,2.00mmol,2.0eq),and7MNH3/MeOH(429muL,1.50mmol,1.5eq.).Thesolutionwasstirredatroomtemperaturefor24hoursthenpouredoverwaterandtheaqueouslayerextractedwithEtOAc(320mL),thecombinedorganiclayerswashedwithbrine(25mL),driedwithNa2SO4andconcentratedinvacuo.TheresiduewaspurifiedbyFCC(gradient50%EtOAc/hexanes to 80% EtOAc/hexanes) to give 2-amino-3-methylbenzamide (90.0 mg,0.599mmol,60%)asawhiteamorphoussolid;mp:144-146C,lit.144-145C.
60% With N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20℃; for 6h; To a stirred solution of 2-amino-3-methyl-benzoic acid (0.5 g, 3.31 mmol) in THF (15 mL),EDC.HCl (0.948 g, 4.97 mmol), HOBt·NH3 (0.745 g, 4.97 mmol) and DIPEA (1.76 mL, 9.93mmol) were added at RT and stirred for 6 h (TLC indicates complete conversion of startingmaterial). The reaction mixture was diluted with water (30 mL) and extracted with EtOAc (3x 100 mL). The combined organic extracts were washed with water (2 x 50 mL), brine (40mL), dried over Na2S04 and concentrated under reduced pressure to give the crude residue The crude material was purified by column chromatography (100-200 silica gel, 20 g, 50%EtOAc-Hexane) to afford 2-amino-3-methyl-benzamide (0.3 g, 60%) as a white solid.LCMS: m/z: 151.09 [M+H] +.

  • 12
  • [ 4389-45-1 ]
  • [ 19181-54-5 ]
  • [ 1332493-28-3 ]
  • [ 1332493-36-3 ]
  • [ 1332493-35-2 ]
  • 13
  • NH3/MeOH [ No CAS ]
  • [ 4389-45-1 ]
  • [ 1885-32-1 ]
YieldReaction ConditionsOperation in experiment
63% With DIEA; benzotriazol-1-ol; In N,N-dimethyl-formamide; Step A: To solution of 2-amino-3-methylbenzoic acid (4.0 g, 26.5 mmol) in degassed DMF (40 mL) were added HOBt (4.28 g, 31.7 mmol), DIEA (5.52 mL, 31.7 mmol), and 2N NH3/MeOH (19 mL, 37.1 mmol). The solution was stirred at room temperature for 16 hrs, then. the mixture was concentrated under reduced pressure and the residue was purified by silica gel chromatography eluting with 10-60% EtOAc/hexanes to afford 2-amino-3-methylbenzamide as a solid (2.52 g, 63%). 1H NMR (300 MHz, DMSO-d6) delta2.07 (s, 3H), 6.40-6.47 (m, 3H), 7.06 (m, 2H), 7.42 (d, 1H), 7.72 (br d, 1H).
  • 14
  • [ 4389-45-1 ]
  • [ 503-38-8 ]
  • [ 66176-17-8 ]
YieldReaction ConditionsOperation in experiment
6.51 g In 1,4-dioxane; at 20 - 25℃; Step C: Preparation of 8-Methyl-2H-3,1-benzoxazine-2,4(1H)-dioneTo a solution of 2-amino-3-methylbenzoic acid (6 g) in dry 1,4-dioxane (50 mL) was added dropwise a solution of trichloromethyl chloroformate (8 mL) in dry 1,4-dioxane (25 mL), with ice water cooling to keep the reaction temperature below 25 C. A white precipitate began to form during the addition. The reaction mixture was stirred at room temperature overnight. The precipitated solids were removed by filtration and washed with 1,4-dioxane (2×20 mL) and hexane (2×15 mL) and air-dried to yield 6.51 g of off-white solid. 1H NMR (DMSO-d6) delta 2.33 (s, 3H), 7.18 (t, 1H), 7.59 (d, 1H), 7.78 (d, 1H), 11.0 (br s, 1H).
In 1,4-dioxane; at 25℃; Step C: Preparation of8-Methyl-2H-3, 1 -benzoxazine-2,4(1 H)-dione To a solution of 2-amino-3-methylbenzoic acid (6 g) in dry1 ,4-dioxane (50 mL) was added dropwise a solution oftrichloromethyl chloroformate (8 mL) in dry 1 ,4-dioxane (25 mE), with ice-water cooling to keep the reaction temperature below 25 C. A white precipitate began to form during the addition. The reaction mixture was stirred at room temperature overnight. The precipitated solids were removed by filtration and washed with 1 ,4-dioxane (2x20 mE) and hexane (2x15 mE) and air-dried to yield 6.51 g of off-white solid.?H NMR (DMSO-d5) oe 2.33 (s, 3H), 7.18 (t, 1H), 7.59 (d, 1H), 7.78 (d, 1H), 11.0 (br s, 1H).
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2-Amino-6-methylbenzoic acid

Similarity: 0.98

Chemical Structure| 50419-58-4

[ 50419-58-4 ]

2-Amino-3,4-dimethylbenzoic acid

Similarity: 0.96

Chemical Structure| 39622-79-2

[ 39622-79-2 ]

2-Aminoisophthalic acid

Similarity: 0.96

Chemical Structure| 15089-51-7

[ 15089-51-7 ]

2-Amino-4,5-dimethylbenzoic acid

Similarity: 0.96

; ;