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CAS No. : | 623-04-1 | MDL No. : | MFCD00014782 |
Formula : | C7H9NO | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AXKGIPZJYUNAIW-UHFFFAOYSA-N |
M.W : | 123.15 | Pubchem ID : | 69331 |
Synonyms : |
|
Chemical Name : | (4-Aminophenyl)methanol |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With Co3O4 nanoparticles; at 20℃; for 0.2h;Green chemistry; | General procedure: In a round-bottomed flask (25 mL) equipped with a magnetic stirrer, a mixture of aniline (0.093 g, 1 mmol) and Co3O4 (0.006 g) was prepared. Acetic anhydride (0.102, 1 mmol) was then added to the reaction mixture and stirring was continued at room temperature for 3 min. The progress of the reaction was followed by TLC. After the reaction completion, the products was extracted with EtOAc and filtered to remove Co3O4. The organic solvent was then washed with H2O (2 x 10 mL) and saturated NaHCO3 solution and then dried over anhydrous Na2SO4. The solvent was removed under vacuum to afford the pure product. |
91% | In neat (no solvent); at 20℃; for 0.1h; | General procedure: Alcohol, phenol, and/or amine (1 mmol) were added to amixture of the ZnAl2O4SiO2 nanocomposite (100 mg) andacetic anhydride (1 mmol). The mixture was stirred at 75 C(for alcohols and phenols) or at room temperature (for amines)for a time. The progress of the reaction was monitored by TLCand/or GC-MS. When the reaction was completed, ethyl acetate(10 mL) was added and the mixture was filtered to separate offthe catalyst. The catalyst was washed twice with 7.5 mL ethylacetate. The combined organic phases were washed with a10% solution of NaHCO3 and then dried over MgSO4. The solventwas removed to yield the product. If further purificationwas needed, the product was passed through a short column ofsilica gel. All products were characterized on the basis ofGC-MS, FT-IR, and 1H-NMR spectral data by comparing thesespectra with those of standard samples or literature data. |
91% | In water; at 50℃; for 0.15h; | General procedure: In a round-bottom flask (10 mL) equipped with a magnetic stirrer, a mixture of PhNH2(1 mmol, 0.093 g) and H2O(3 mL) in oil bath (50 C) was prepared. Magnetically recyclable nanoparticles of Fe3O4/Cu (0.05 mmol) was then added, and the mixture was stirred for 1 min under oil bath conditions. Addition of Ac2O(1 mmol, 0.102 g) to the prepared mixture was followed by stirring for 3 min at 50 C. After completion of the reaction, the copper nanocatalyst was separated by an external magnet and the mixture was extracted with EtOAc (3 × 8 mL). Organic layers were then dried over anhydrous sodium sulfate. Evaporation of the solvent under reduced pressure affords the pure acetanilide in 95% yield (0.128 g, Table 2, entry 1). |
In ethanol; water; at 70℃; | General procedure: In a round-bottom flask (25 mL), a solution of nitrobenzene (0.123 g, 1 mmol) in H2O-EtOH (1.5:0.5 mL) was prepared. Magnetically, nanoparticles of NiFe2O4(at)Cu (0.15 g) were added, and the resulting mixture was stirred for 5 min. Afterward,NaBH4 (0.094 g, 2.5 mmol) was added and the resulting mixture was continued to stirring for 1 min at 70 C. After reduction of nitrobenzene to aniline (monitored by TLC), Ac2O (0.204 g, 2 mmol) was added and the resulting mixture was stirred for 1 min at 70 C. The nanocatalyst was separated by an external magnet, and the mixture was extracted with EtOAc (3 × 5 mL). The organic layer was dried over anhydrous Na2SO4. Evaporation of the solvent affords the pure acetanilide in 95% yield (0.128 g, Table 3,entry 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In tetrahydrofuran; thionyl chloride; | Preparation of 3,5-dichloro-N-(4-hydroxymethyl-phenyl)-isonicotinamide: A suspension of <strong>[13958-93-5]3,5-dichloroisonicotinic acid</strong> (128 mg, 0.667 mmol) in thionyl chloride (2 mL) was heated at reflux for 2 h, then concentrated. To the residue was added 4-aminobenzyl alcohol (123 mg, 0.999 mmol) and THF (2.2 mL), and the mixture was stirred at room temperature for 19 h. The mixture was filtered, and the filtrate was concentrated to give a yellow foam (125 mg, 63%). 1H NMR (CD3OD) delta 4.60 (s, 2H), 7.38 (d, 2H, J=8.7 Hz), 7.63 (d, 2H, J=8.4 Hz), 8.66 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To a solution of 1H-Indole-3-carboxylic acid, 1-(phenylmethyl)-(CAS 27018-76-4) (1.0 g, 3.7 mmol) in DCM (10 mL) was added oxalyl chloride (0.950 mgs, 7.5 mmol) followed by the addition of DMF (3 drops) at room temperature. The solvent was removed under reduced pressure and gave the crude product. To the crude material in DCM (10 mL) was added (4-aminophenyl)methanol, (0.478 mgs, 3.8 mmol), followed by triethylamine (0.98 ml, 7.0 mmol). The reaction mixture was stirred at room temperature overnight. The reaction mixture was quenched with water and extracted in DCM. The organic layer was separated and dried over magnesium sulphate and the solution was filtered. The filtrate was evaporated under reduced pressure to give the crude product, which was purified on a column (MPLC) using DCM:MeOH and gave Intermediate 7 (550 mgs).1H NMR (300 MHz, CD3OD) delta: 8.48 (s, 1H), 8.51-8.62 (m, 2H), 7.24-7.33 (m, 7H), 7.82 (d, J=8.1 Hz, 2H), 8.95 (d, J=8.1 Hz, 2H), 5.41 (s, 2H), 4.61 (s, 2H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With ammonium iodide; hydrazine; at 50℃; for 18h; | Purification by column chromatography (ethyl acetate/hexane = 2/1) provided a white solid product. Yield 116 mg (94%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; In dichloromethane; at 20℃; for 12h; | A solution of <strong>[145038-49-9]Fmoc-Glu-OMe</strong> (II, 425 mg, 1 mmol) and 4-aminobenzyl alcohol (III, 123 mg, 1 mmol) was dissolved in 20 ml of methylene chloride,2-ethoxy-1-ethoxycarbonyl-12-dihydroquinoline (EEDQ) (296 mg, 1.2 mmol) was added,The reaction was stirred at room temperature for 12 hours.The reaction solution was diluted with 50 ml of methylene chloride,The reaction was quenched by the addition of 1 N of dilute hydrochloric acid.The organic layer was washed successively with saturated sodium bicarbonate,And saturated saline, the wash 3 times,Dried over anhydrous sodium sulfate,Filtration, concentration,Silica gel column chromatography (petroleum ether: ethyl acetate = 2: 1)To give light yellow solid IV (424 mg, 80%). |
74% | With 4-methyl-morpholine; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 3h; | A GGT targeted prodrug was synthesized via the following Scheme 3. Fmoc and methyl protected L-glutamic acid was coupled with p-aminobenzyl alcohol from gamma-carboxylic acid followed by bromination. The brominated intermediate was then coupled to diethyldithiocarbamate which was then deprotected to yield the final desired product. A) p-Aminobenzyl alcohol, HBTU, 4percent NMM in DMF, 3h, rt, 74percent; B) PBr3, Dry THF, 3 h, 0 °C, 43percent; C)(i) Sodium diethyldithiocarbamate, Dry THF, 12 h, rt , 48percent (ii) LiOH in THF and H20, 30 min, rt, D) 20percent piperidine in DMF, 1 h, rt, 48percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With 10-methyl-9-(2,4,6-trimethylphenyl) acridinium tetrafluoroborate; In acetonitrile; at 20℃; for 5h;Irradiation; | In air, p-aminobenzyl alcohol (0.2 mmol, 27 mg) was dissolved in acetonitrile (2 mL), and then Mes-Acr-MeBF4 (2 mol%, 2 mg) and thioacetic acid (0.4 mmol, 30 mg) were added. The mixture was stirred for 5 hours at room temperature under a 36W blue LED. The mixture was quenched with water (2 mL) and then extracted with EtOAc (3 x 4 mL). The organic phase was washed with brine, dried over Na 2 SO 4 and spin-dried, and then separated by column chromatography to obtain 26 mg of a white solid product with a yield of 79%. |
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