3-Methoxy-5-nitrobenzotrifluoride → 5-(Trifluoromethyl)-m-anisidine

HRID 873079Notes

Reaction equation

HRID 873079 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[C:5]([N+:13]([O-])=O)[CH:4]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1)[NH2:13]

Participants

4

Reactant 1

HCID 5205973-Methoxy-5-nitrobenzotrifluoride

Product 1

HCID 6056715-(Trifluoromethyl)-m-anisidineYield 98.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-methoxy-3-nitro-5-(trifluoromethyl)benzene (8.50 g, 38.4 mmol) and 10% Pd/C (2.00 g, 1.88 mmol) in methanol (40 mL) was stirred under hydrogen balloon at rt for 24 h, and filtered through a pad of celite and concentrated to give the title product (7.2 g) as an orange solid

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-a3ab619509904ebf8c78229ba033dc06
Source dataset
uspto-grants-2015_03
Patent number
US08975400B2

Reaction notes

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