2-Methyl-3-nitrobenzyl alcohol → (3-Amino-2-methylphenyl)methanol

HRID 2051237Notes

Reaction equation

HRID 2051237 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:11][OH:12]>CO.[Ni]>[NH2:8][C:7]1[C:2]([CH3:1])=[C:3]([CH2:11][OH:12])[CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 1

HCID 902892-Methyl-3-nitrobenzyl alcohol

Product 1

HCID 577175(3-Amino-2-methylphenyl)methanolYield 90.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-methyl-3-nitrobenzenemethanol (10.0 g, 59.8 mmol) in methanol is treated with Raney Nickel and shaken under hydrogen gas (50 psi) in a Parr Shaker. The solution is filtered through Celite and evaporated. Recrystallization of the residue from isopropyl ether gives pure 3-amino-2-methylbenzenemethanol (7.4 g, 90%), mp=106-108° C.

Workup

  1. filtrationThe solution is filtered through Celite
  2. customevaporated
  3. customRecrystallization of the residue from isopropyl ether

Sources & evidence

ORD record
ord-d8b1fd7509a24476979881ec20c3dea0
Source dataset
uspto-grants-1991_05
Patent number
US05017604

Reaction notes

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