5-Methoxy-2-nitrobenzaldehyde → (2-Amino-5-methoxyphenyl)methanol

HRID 463059

Reaction equation

HRID 463059 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([N+:11]([O-])=O)=[C:7]([CH:10]=1)[CH:8]=[O:9].[H][H]>CO.[Ni]>[NH2:11][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:10][C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 2

HCID 2303715-Methoxy-2-nitrobenzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 13756678(2-Amino-5-methoxyphenyl)methanol

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A quantity of 181.2 gm (1 mol) of 5-methoxy-2-nitrobenzaldehyde (prepared by methylation of 2-nitro-5-hydroxy-benzaldehyde with methyl iodide/potassium tert.-butoxide in dimethylsulfoxide) is dissolved in 1.8 liters of methanol, mixed with 50 gm of Raney nickel, and hydrogenated at ambient temperature and at 5 bar. After ten hours, the hydrogen uptake has ended. The catalyst is removed by suction filtration, and the methanol is distilled off.

Workup

  1. customhydrogenated at ambient temperature
  2. waitAfter ten hours
  3. customThe catalyst is removed by suction filtration
  4. distillationthe methanol is distilled off

Sources & evidence

ORD record
ord-03aee2ce438b454aa75f4a46a9749cfa
Source dataset
uspto-grants-1985_05
Patent number
US04518597

Linked notes

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