4-Methyl-3-nitroanisole → 5-Methoxy-o-toluidine

HRID 1505307

Reaction equation

HRID 1505307 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[N+:10]([O-])=O>CO.[Pd]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[NH2:10]

Participants

4

Reactant 1

HCID 871374-Methyl-3-nitroanisole

Product 1

HCID 995005-Methoxy-o-toluidineYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-methyl-4-(methyloxy)-2-nitrobenzene (20.0 g, 119.8 mmol) and Pd/C (10%, 3 g) in methanol (100 mL) was stirred under H2 atmosphere at room temperature overnight. The mixture was filtered through a pad of celite and the filtrate was evaporated under vacuum to afford the title compound as a solid (16.1 g).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-8e86203e25ed4fb299a6b6dbffeed19f
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Linked notes

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