2-Methyl-3-nitroanisole → 3-Methoxy-2-methylaniline

HRID 1505346Notes

Reaction equation

HRID 1505346 reaction equation
[CH3:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12]>CO.[Pd]>[CH3:1][C:2]1[C:3]([O:11][CH3:12])=[CH:4][CH:5]=[CH:6][C:7]=1[NH2:8]

Participants

4

Reactant 1

HCID 785542-Methyl-3-nitroanisole2×

Product 1

HCID 118048223-Methoxy-2-methylanilineYield 95.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methyl-1-(methyloxy)-3-nitrobenzene (Intermediate 57, 1.67 g) in methanol (50 mL) was added Pd/C (10%, 50 mg) and the reaction mixture was stirred under H2 atmosphere for 1 hour. The mixture was filtered through a pad of celite. Evaporation afforded the title compound as a solid (1.31 g).

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customEvaporation

Sources & evidence

ORD record
ord-70c9384926474ff19fbee7ce88f6f870
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

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