Preparation of 3-amino-2-methylbenzyl alcohol_industrial additives

Background and overview[1]

3-Amino-2-methylbenzyl alcohol can be used as a pharmaceutical synthesis intermediate. If 3-amino-2-methylbenzyl alcohol is inhaled, move the patient to fresh air; if skin contact occurs, take off contaminated clothing, rinse the skin thoroughly with soap and water, and seek medical attention if you feel unwell; if In case of eye contact, separate eyelids, rinse with running water or saline, and seek medical attention immediately; if ingested, rinse mouth immediately, do not induce vomiting, and seek medical attention immediately.

Preparation[1]

The preparation of 3-amino-2-methylbenzyl alcohol is as follows:

The specific steps are as follows: To a stirred solution of (2-methyl-3-nitro-phenyl)-methanol (13) (100 mg, 0.598 mmol) in EtOH (5 mL) and water (1 mL) was added Iron powder (183 mg, 3.29 mmol) and ammonium chloride (22 mg, 0.419 mmol), and the resulting mixture was refluxed for 2 hours. The reaction mixture was then warmed to room temperature and filtered through a bed of Celite. The filtrate was diluted with EtOAc, washed with water, dried over sodium sulfate and concentrated under reduced pressure to obtain 3-amino-2-methylbenzyl alcohol (70 mg, 85%) as a yellow gum.

Application

3-Amino-2-methylbenzyl alcohol can be used as an intermediate in pharmaceutical synthesis and can undergo the following reactions:

The specific steps are as follows: Add 0.51mmol) and HATU (290mg, 0.765mmol) of 3-amino-2-methylbenzyl alcohol (70mg, 0.51mmol) to pyridine (1mL) and incubate the reaction mixture at 0°C Stir. 50°C, 16 hours. It was then diluted with EtOAc, washed with 2NHCl, saturated NaHCO3 solution in water, dried over sodium sulfate and concentrated under reduced pressure. The crude product thus obtained was purified by column chromatography (silica, gradient: 25-30% EtOA in hexane) to give the desired compound as an off-white solid (35 mg 18%).

Main reference materials

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TAG: 3-amino-2-methylbenzyl alcohol, application of 3-amino-2-methylbenzyl alcohol, preparation of 3-amino-2-methylbenzyl alcohol,

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