Ammonia → [4-Methoxy-2-(trifluoromethyl)phenyl]methanamine

HRID 1678406Notes

Reaction equation

HRID 1678406 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:4]=1.[NH3:15].[H][H]>[Ni].CO>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH2:7][NH2:15])=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:4]=1

Participants

6

Reactant 3

HCID 222AmmoniaHCID 27782864-Methoxy-2-(trifluoromethyl)benzaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 43138648[4-Methoxy-2-(trifluoromethyl)phenyl]methanamineYield 67.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a mixture of 4-(methyloxy)-2-(trifluoromethyl)benzaldehyde (14 g, 65 mmol, 1.0 equiv), aqueous NH3 (25-28%, 370 mL, 5.20 mol, 80 equiv), and MeOH (300 mL) was added Raney-Ni (3.8 g, 65 mmol, 1.0 equiv). The flask was fitted with a hydrogen balloon, and the mixture was stirred for 7 days at room temperature. The reaction mixture was filtered through a celite cake, and the filtrate was concentrated. The residue was purified by HPLC to afford 9 g (67%) of the title compound as the trifluoroacetate salt. MS (ES+): m/e 206 [M+H]+. 1H NMR (400 MHz, DMSO-D6) 7.6 (d, 1H), 7.3 (d, 1H), 7.2 (s, 1H), 4.1 (s, 2H), 3.8 (s, 3H)

Workup

  1. filtrationThe reaction mixture was filtered through a celite cake
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by HPLC

Sources & evidence

ORD record
ord-fc377246a8b049f0a1b89eab100e86c0
Source dataset
uspto-grants-2011_08
Patent number
US08008483B2

Reaction notes

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