3-Methyl-4-nitrobenzyl alcohol → (4-Amino-3-methylphenyl)methanol

HRID 1746668Notes

Reaction equation

HRID 1746668 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[N+:10]([O-])=O)[CH2:5][OH:6].[H][H]>CO.[Pd]>[NH2:10][C:9]1[CH:8]=[CH:7][C:4]([CH2:5][OH:6])=[CH:3][C:2]=1[CH3:1]

Participants

5

Reactant 2

HCID 5913603-Methyl-4-nitrobenzyl alcoholHCID 178418361HCID 178418361, compound

Product 1

HCID 1514189(4-Amino-3-methylphenyl)methanolYield 91.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3-methyl-4-nitrobenzyl alcohol (Aldrich; 2.000 g; 12.0 mmol) in MeOH (90 ml) is passed through the H-Cube flow hydrogenator fitted with a 10 mol % Pd/C catalyst cartridge (30×4 mm) heated to 25° C. with the full hydrogen option enabled. The flow rate is set at 1 mL/min. Solvent was removed to give the title compound (1.50 g, 91.4%) without further purification.

Workup

  1. customSolvent was removed

Sources & evidence

ORD record
ord-c376283c46d744948e52ec2bf684c5e7
Source dataset
uspto-grants-2015_10
Patent number
US09150519B2

Reaction notes

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