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[ CAS No. 612-62-4 ] {[proInfo.proName]}

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Chemical Structure| 612-62-4
Chemical Structure| 612-62-4
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Product Citations

Product Citations

Mohammad B. Teimouri ; Irena Deperasińska ; Matt Rammo , et al. DOI:

Abstract: A straightforward route to 1,4-dihydropyrrolo[3,2-b]pyrroles comprised of two electron-withdrawing quinoline or tetrazolo[1,5-a]quinoline scaffolds has been developed. The versatile multicomponent reaction affording 1,4-dihydropyrrolo[3,2-b]pyrroles combined with intramolecular direct arylation enables assembly of these products in just three steps from anilines with overall yields exceeding 30%. The planarized, ladder-type heteroacenes possess up to 14 conjugated rings. These nominally quadrupolar materials exhibit efficient fluorescence with wavelengths spanning most of the visible spectrum from green–yellow for the dyes possessing biaryl bridges and orange–red for the fully fused systems. In many cases, the fluorescence quantum yields are large, the solvatofluorochromic effects are strong, and the fluorescence is maintained even in crystalline state. Analysis of the electronic structure of these molecular architectures using quantum chemical methods suggests that the character and position of the flanking heterocycle determine the shape of HOMO and LUMO and their extension to N-aryl substituents, influencing the values of molar absorption coefficient. An experimental study of the two-photon absorption (2PA) properties has revealed that it occurs in the 700–800 nm range with apparent deviation from the Laporte parity selection rule, which may be attributed to Hertzberg–Teller contribution to vibronically allowed 2PA transition.

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Product Details of [ 612-62-4 ]

CAS No. :612-62-4 MDL No. :MFCD00006741
Formula : C9H6ClN Boiling Point : -
Linear Structure Formula :- InChI Key :OFUFXTHGZWIDDB-UHFFFAOYSA-N
M.W : 163.60 Pubchem ID :11928
Synonyms :

Calculated chemistry of [ 612-62-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 10
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 1.0
Num. H-bond donors : 0.0
Molar Refractivity : 46.75
TPSA : 12.89 ?2

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.37 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.11
Log Po/w (XLOGP3) : 2.71
Log Po/w (WLOGP) : 2.89
Log Po/w (MLOGP) : 2.42
Log Po/w (SILICOS-IT) : 3.13
Consensus Log Po/w : 2.65

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -3.23
Solubility : 0.0954 mg/ml ; 0.000583 mol/l
Class : Soluble
Log S (Ali) : -2.63
Solubility : 0.38 mg/ml ; 0.00232 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.31
Solubility : 0.00807 mg/ml ; 0.0000493 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 612-62-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 612-62-4 ]

* 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 [ 612-62-4 ]

[ 612-62-4 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 612-62-4 ]
  • [ 74-89-5 ]
  • [ 52430-43-0 ]
  • 2
  • [ 612-62-4 ]
  • [ 13067-94-2 ]
  • [ 4225-86-9 ]
YieldReaction ConditionsOperation in experiment
14%; 54% Pure H2SO4 was added onto 1 equiv of 29 at 0 C. 3 equiv of 65% HNO3 were then added dropwise and the reaction mixture was stirred at rt for 1 h. After the reaction mixture was poured into water, the solution was neutralized with Na2CO3 and extracted twice with dichloromethane. The organic layer was washed with water, dried over anhydrous Na2SO4 and evaporated in vacuo.Compound 30 was obtained, after purification by column chromatography (eluent: cyclohexane-ethyl acetate 8:2), as a white solid in 54% yield; mp 152 C, Lit: 149 C [40]. 1H NMR (200 MHz, CDCl3) delta: 7.52-7.56 (d, J = 8.6 Hz, 1H), 7.60-7.68 (m, 1H), 8.02-8.11 (m, 2H), 8.20 (d, J = 8.6 Hz, 1H). 13C NMR (50 MHz, CDCl3) delta: 124.6 (CH), 124.9 (CH), 125.8 (CH), 127.6 (C), 131.8 (CH), 138.6 (CH), 139.0 (C), 147.3 (C), 153.6 (C).Compound 31 was obtained, after purification by column chromatography (eluent: cyclohexane-ethyl acetate 8:2), as a pale yellow solid in 14% yield; mp 134 C, Lit: 133-134 C [41]. 1H NMR (200 MHz, CDCl3) delta: 7.63 (d, J = 9.2 Hz, 1H), 7.80-7.88 (m, 1H), 8.34 (d, J = 8.5 Hz, 1H), 8.40 (dd, J = 1.1 and 7.7 Hz, 1H), 8.99 (d, J = 9.2 Hz, 1H). 13C NMR (50 MHz, CDCl3) delta: 119.9 (C), 124.9 (CH), 125.4 (CH), 128.8 (CH), 134.9 (CH), 135.5 (CH), 145.4 (C), 148.0 (C), 152.5 (C).
14%; 50% With sulfuric acid; nitric acid; In water; at 0 - 20℃; for 2.0h; General procedure: H2SO4 (98%) was added onto 1 equiv. of the quinoline derivatives, cooled with an ice bath. 5 equiv. of 65% HNO3 were then added dropwise at 0 C and the reaction mixture was stirred at rt for 1-4 h. The reaction mixture was successively poured into ice, neutralized with NaOH and extracted three times with dichloromethane. The organic layer was washed with water, dried over anhydrous Na2SO4 and evaporated in vacuo. The crude residue was purified by chromatography on silica gel using adapted eluent and recrystallized if necessary to give compounds 1, 4, 6, 12, 15, 17 and 18. 8-nitroquinoline 1 (C9H6N2O2) was purified by chromatography on silica gel using dichloromethane as an eluent, separated from its 5-nitro isomer and isolated to yield a pale yellow solid (35%, 2.7 mmol, 470 mg).
  • 3
  • [ 123-39-7 ]
  • [ 612-62-4 ]
  • [ 52430-43-0 ]
  • 4
  • [ 612-62-4 ]
  • HNO3+H2SO4 [ No CAS ]
  • [ 13067-94-2 ]
  • [ 4225-86-9 ]
  • 5
  • [ 13220-33-2 ]
  • [ 612-62-4 ]
  • [ 108-20-3 ]
  • [ 117449-88-4 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; n-butyllithium; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; chloroform; water; toluene; 2-(2-Chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-b]-quinolin-5(4H)-one To 21.3 ml (0.15 mole) of diisopropylamine in 300 ml of tetrahydrofuran at -70° C. was added dropwise, at a rate to keep the temperature between -70° and -60° C., 61.1 ml of 2.7M n-butyllithium (0.16 mole). The temperature was maintained at -70° C.+-3° C. for 20 minutes. A solution of 2-chloroquinoline in 60 ml of tetrahydrofuran was added dropwise at a rate such that temperature remained between -70° and -60° C. After 20 minutes, the darkened reaction solution was poured onto a large excess of dry ice. The solvent was evaporated with a stream of air. The residue was taken up in 300 ml of water, made basic with dilute aqueous sodium hydroxide and washed with 3*50 ml of isopropyl ether. The aqueous phase was filtered and treated with dilute hydrochloric acid to ~pH 4-5, at which time a copious precipitate formed. The precipitate was collected and the filtrate reacidified yielding more precipitate. The precipitates were combined and washed with water, isopropyl alcohol, and isopropyl ether. Approximately 15.4 g (61.5percent) of off-white crystals were collected. To a suspension of 4.0 g of 60percent sodium hydride in oil (0.10 mole) in 100 ml tetrahydrofuran heated to reflux was added a solution of 5.5 g (0.048 mole) of N-methyl-3-pyrrolidinol and 10 g (0.048 mole) of the above prepared 2-chloro-3-quinolinecarboxylic and in 50 ml of tetrahydrofuran at such rate as to maintain good reflux. Reflux was maintained for 1.5 hr and the reaction mixture cooled. The solvent was removed by rotary evaporation yielding 26 g crude product. The entire crude product from above was suspended in 150 ml chloroform and hydrogen chloride bubbled in until pH of 5.76 was reached (note: after hydrogen chloride addition ceased, the pH continued to lower to 1.7). To this suspension was added 25.0 g (0.096 mole) of triphenylphosphine and 25 g of carbon tetrachloride. After 45 min, an additional 10 g (0.038 mole) of triphenylphosphine and 10 g of carbon tetrachloride was added. After 30 minutes, the heat was removed and the reaction driven to completion by dropwise addition of 20 ml of triethylamine. The reaction mixture was extracted with 3*50 ml of 3N hydrochloric acid. The aqueous extracts were combined, washed with 2*50 ml chloroform, made basic with concentrated sodium hydroxide and extracted with 3*50 ml of chloroform. The organic extracts were combined and concentrated by rotary evaporation. The syrupy residue was taken up in 100 ml of toluene and treated with activated charcoal. The toluene was removed by rotary evaporation and the syrupy residue crystallized from isopropyl alcohol, giving 1.5 g (11percent) of white crystals, m.p. 133°-134° C. Analysis: Calculated for C15 H15 N2 Cl: C, 61.97; H, 5.20; N, 9.63. Found: C, 61.73; H, 5.18 N, 9.54.
With hydrogenchloride; n-butyllithium; triethylamine; diisopropylamine; triphenylphosphine; In tetrahydrofuran; tetrachloromethane; chloroform; water; toluene; 2-(2-Chloroethyl)-2,3-dihydro-4-methyl-1,4-oxazepino[6,7-b]-quinolin-5(4H)-one To 21.3 ml (0.15 mole) of diisopropylamine in 300 ml of tetrahydrofuran at -70° C. was added dropwise, at a rate to keep the temperature between -70° and -60° C., 61.1 ml of 2.7M n-butyllithium (0.16 mole). The temperature was maintained at -70° C.+-3° C. for 20 minutes. A solution of 2-chloroquinoline in 60 ml of tetrahydrofuran was added dropwise at a rate such that temperature remained between -70° and -60° C. After 20 minutes, the darkened reaction solution was poured onto a large excess of dry ice. The solvent was evaporated with a stream of air. The residue was taken up in 300 ml of water, made basic with dilute aqueous sodium hydroxide and washed with 3*50 ml of isopropyl ether. The aqueous phase was filtered and treated with dilute hydrochloric acid to ~pH 4-5, at which time a copious precipitate formed. The precipitate was collected and the filtrate reacidified yielding more precipitate. The precipitates were combined and washed with water, isopropyl alcohol, and isopropyl ether. Approximately 15.4 g (61.5percent) of off-white crystals were collected. To a suspension of 4.0 g of 60percent sodium hydride in oil (0.10 mole) in 100 ml tetrahydrofuran heated to reflux was added a solution of 5.5 g (0.048 mole) of N-methyl-3-pyrrolidinol and 10 g (0.048 mole) of the above prepared 2-chloro-3-quinolinecarboxylic and in 50 ml of tetrahydrofuran at such rate as to maintain good reflux. Reflux was maintained for 1.5 hr and the reaction mixture cooled. The solvent was removed by rotary evaporation yielding 26 g crude product. The entire crude product from above was suspended in 150 ml chloroform and hydrogen chloride bubbled in until pH of 5.76 was reached (note: after hydrogen chloride addition ceased, the pH continued to lower to 1.7). To this suspension was added 25.0 g (0.096 mole) of triphenylphosphine and 25 g of carbon tetrachloride. After 45 min, an additional 10 g (0.038 mole) of triphenylphosphine and 10 g of carbon tetrachloride was added. After 30 minutes, the heat was removed and the reaction driven to completion by dropwise addition of 20 ml of triethylamine. The reaction mixture was extracted with 3*50 ml of 3N hydrochloric acid. The aqueous extracts were combined, washed with 2*50 ml chloroform, made basic with concentrated sodium hydroxide and extracted with 3*50 ml of chloroform. The organic extracts were combined and concentrated by rotary evaporation. The syrupy residue was taken up in 100 ml of toluene and treated with activated charcoal. The toluene was removed by rotary evaporation and the syrupy residue crystallized from isopropyl alcohol, giving 1.5 g (11percent) of white crystals, m.p. 133°-134° C. Analysis: Calculated for C15 H15 N2 O2 Cl: C, 61.97; H, 5.20; N, 9.63. Found: C, 61.73; H, 5.18; N, 9.54.
  • 6
  • [ 612-62-4 ]
  • 5-(2-quinolinyloxy)-2-pyridine carboxaldehyde [ No CAS ]
  • [ 31191-08-9 ]
  • [ 110-53-2 ]
  • [ 693-25-4 ]
  • 2-[2-(1-Hydroxyhexyl)-5-pyridyloxy]quinoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
3.6 g (35%) With ammonium chloride; In tetrahydrofuran; hexane; ethyl acetate; N,N-dimethyl-formamide; EXAMPLE 6 2-[2-(1-Hydroxyhexyl)-5-pyridyloxy]quinoline To a suspension of sodium hydride (3.6 g, 0.15 mol) in dry DMF (150 ml) containing 2-chloroquinoline (24.5 g, 0.15 mol) was added dropwise a solution of <strong>[31191-08-9]5-hydroxypyridine-2-carboxaldehyde</strong> (18.5 g, 0.15 mol) in dry DMF (75 ml). The solution was stirred vigorously with a mechanical stirrer. After the addition was complete (90 min.), the reaction was heated to about 90° C. for 12 hours. Most of the DMF was removed, and the residue was carefully poured into cold water. The aqueous solution was extracted with ethyl acetate (4*30 ml), and the organic extract was washed with water, brine, and then dried over MgSO4. All volatiles were removed to leave the crude aldehyde intermediate (26 g) which was pure enough to be used in the next step. To a cold (-30° C.) solution of 5-(2-quinolinyloxy)-2-pyridine carboxaldehyde (8 g, 0.032 mol) in dry THF (125 ml) was added a solution of pentylmagnesium bromide (prepared from 4.83 g (0.032 mol) of 1-bromopentane and 0.78 g (0.032 mol) of Mg turnings in THF (60 ml). After the addition of the Grignard reagent was complete (-45° C.), the solution was stirred at this temperature for 90 minutes, and allowed to slowly warm up to room temperature in about 2 hours. The reaction was quenched by adding a saturated solution of ammonium chloride. The clear organic layer was decanted, and most of the volatiles were removed. The residue was taken up in ethyl acetate, and then washed with water, brine, and dried over MgSO4. After removal of the ethyl acetate the crude residue (7.7 g) was purified by HPLC (silica gel; 25percent ethyl acetate in hexane) to give 3.6 g (35percent) of pure product.
  • 7
  • [ 612-62-4 ]
  • [ 227960-12-5 ]
  • 3-methoxycarbonyl-5-methyl-1-(quinol-2-yl)-1H-indole [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.63 g (11.8 [MMOL)] of potassium carbonate are added at [25C] under an argon atmosphere to 0.895 g (4.73 [MMOL)] of [3-METHOXYCARBONYL-5-METHYL-1 H-INDOLE] in 10 cm3 of dimethyl sulphoxide. After stirring at [25C] for 0.5 hour, 0.774 g (4.73 [MMOL)] of 2-chloroquinoline is added. After stirring at [100C] for 48 hours, the reaction mixture is cooled and diluted with 100 cm3 ethyl acetate and then washed with 3 times 50 cm3 of water and 25 cm3 of saturated aqueous sodium chloride solution. After separating the phases by settling, the organic phase is dried over anhydrous magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa) to give 1.2 g of a residue which is recrystallised under hot conditions from 30 cm3 of cyclohexane and 6 cm3 of ethyl acetate to give 0. 8 g of [3-METHOXYCARBONYL-5-METHYL-] [1-(QUINOL-2-YL)-1 H-INDOLE] in the form of a white solid melting at [143C.]
  • 8
  • [ 612-62-4 ]
  • [ 13067-94-2 ]
YieldReaction ConditionsOperation in experiment
19% With sulfuric acid; nitric acid; at 0 - 40℃; for 0.833333h; A solution of nitric acid (16 mL) and sulfuric acid (8 mL) was added over period of 20 min to a solution of 2-chloroquinoline (61.1 mmol) in sulfuric acid (150 mL) at 0 C. The reaction mixture was heated at 40 C for 30 min and was quenched with ice water (800 mL). The precipitated solids were collected by filtration and purified by Flash chromatography (20/1 petroleum ether/ethyl acetate) to provide 2-chloro-5-nitroquinoline in 19% yield as a yellow solid.
19% With sulfuric acid; nitric acid; at 0 - 40℃; 20: Synthesis of 2-oxo-l,2-dihydroquinoline-5-sulfonyl chloride.1. Synthesis of 2-chloro-5-nitroquinoline.A solution of nitric acid (16 mL) and sulfuric acid (8 mL) was added over period of 20 min to a solution of 2-chloroquinoline (61.1 mmol) in sulfuric acid (150 mL) at 0 0C. The reaction mixture was heated at 40 0C for 30 min and was quenched with ice water (800 mL). The precipitated solids were collected by filtration and purified by Flash chromatography (20/1 petroleum ether/ethyl acetate) to provide 2-chloro-5-nitroquinoline in 19% yield as a yellow solid.
19% With sulfuric acid; nitric acid; at 0 - 40℃; 1. Synthesis of 2-chloro-5-nitroquinoline.A solution of nitric acid (16 mL) and sulfuric acid (8 mL) was added over period of 20 min to a solution of 2-chloroquinoline (61.1 mmol) in sulfuric acid (150 mL) at 0 0C. The reaction mixture was heated at 40 0C for 30 min and was quenched with ice water (800 mL). The precipitated solids were collected by filtration and purified by Flash chromatography (20/1 petroleum ether/ethyl acetate) to provide 2-chloro-5-nitroquinoline in 19% yield as a yellow solid.
With sulfuric acid; nitric acid; at -10 - 20℃; for 1.33h; To a solution of 12b (5.00 g, 30.6 mmol) in H2SO4 (15 mL) was added HNO3 (2.04 mL, 45.9 mmol) at -10 C and the reaction mixture was stirred at -10 C for 20 min and at room temperature for 1 h. The mixture was poured into crushed-ice, filtered and, washed with water. The obtained crude title compound (5.64 g), which was used in the following reaction without further purification.

  • 9
  • [ 612-62-4 ]
  • [ 17626-75-4 ]
  • [ 1130431-23-0 ]
  • 10
  • [ 612-62-4 ]
  • [ 1196473-37-6 ]
  • [ 1268390-22-2 ]
  • 11
  • [ 612-62-4 ]
  • [ 374790-93-9 ]
  • [ 4637-63-2 ]
YieldReaction ConditionsOperation in experiment
95% With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate; lithium hydroxide; In 1,4-dioxane; water; at 80℃; for 0.5h;Inert atmosphere; General procedure: To a solution of 2-chloroheteroaryl compound 1 (0.50 mmol) in 1,4-dioxane (4.0 mL) were added pinacol boronate 3, 5, or 7 (0.60 mmol), Pd(OAc)2 (1.1 mg, 5.0 mumol), S-Phos (4.1 mg, 10.0 mumol), and 2 M LiOH solution (1.0 mL, 2.0 mmol) at room temperature, and the mixture was stirred for 30 min at 80 C under N2 atmosphere. The reaction was quenched by adding water, and then the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. After filtration, the solvent was removed in vacuo, and the residue was purified by silica-gel column chromatography. The solvent was removed in vacuo, and the residue was triturated with Et2O to give biaryl compounds.
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