3-Methyl-2-nitrophenol → 2-Amino-m-cresol

HRID 1372665Notes

Reaction equation

HRID 1372665 reaction equation
[CH3:1][C:2]1[C:3]([N+:9]([O-])=O)=[C:4]([OH:8])[CH:5]=[CH:6][CH:7]=1>CO.[C].[Pd]>[NH2:9][C:3]1[C:2]([CH3:1])=[CH:7][CH:6]=[CH:5][C:4]=1[OH:8]

Participants

4

Reactant 1

HCID 210263-Methyl-2-nitrophenol

Product 1

HCID 30141382-Amino-m-cresolYield 99%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In methanol (20 ml), 10% palladium-carbon (0.30 g, 20 wt %) was added to 3-methyl-2-nitrophenol (1.50 g, 9.80 mmol) and they were subjected to catalytic hydrogenation for 4 days. From the reaction mixture, an insoluble matter was filtered off through Celite. The filtrate was distilled under reduced pressure to remove the solvent to give 2-amino-3-methylphenol (1.19 g, 99%) as a brown oil.

Workup

  1. filtrationFrom the reaction mixture, an insoluble matter was filtered off through Celite
  2. distillationThe filtrate was distilled under reduced pressure
  3. customto remove the solvent

Sources & evidence

ORD record
ord-ac0b284f0d3447f182bf3af12526ac12
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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