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

HRID 2066717Notes

Reaction equation

HRID 2066717 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([F:15])([F:14])[F:13])[CH:6]=[C:7]([N+:9]([O-])=O)[CH:8]=1>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:12]([F:13])([F:14])[F:15])[CH:6]=[C:7]([CH:8]=1)[NH2:9]

Participants

4

Reactant 1

HCID 5205973-Methoxy-5-nitrobenzotrifluoride

Product 1

HCID 6056715-(Trifluoromethyl)-m-anisidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Hydrogenation of a solution of 3-methoxy-5-nitrobenzotrifluoride (6.19 g, 28 mmol) in MeOH (140 ml) in the presence of Pd—C (0.62 g, 10%), removal of the catalyst by filtration and concentration in vacuo of the resulting filtrate gives the title compound: API-MS: 190 [M-H]−; TLC: Rf=0.7 (EtOAc).

Workup

  1. filtrationby filtration and concentration in vacuo of the resulting filtrate

Sources & evidence

ORD record
ord-22e5658370404eee9096e70750d23855
Source dataset
uspto-grants-2012_10
Patent number
US08293746B2

Reaction notes

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