N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,6-dimethoxy-3-nitrobenzamide → 3-amino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,6-dimethoxy-benzamide

HRID 1967651Notes

Reaction equation

HRID 1967651 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]([F:17])([C:13]([F:16])([F:15])[F:14])[C:9]([F:12])([F:11])[F:10])[CH:5]=[C:4]([CH3:18])[C:3]=1[NH:19][C:20](=[O:34])[C:21]1[C:26]([O:27][CH3:28])=[CH:25][CH:24]=[C:23]([N+:29]([O-])=O)[C:22]=1[O:32][CH3:33]>C(O)C.[Pd]>[NH2:29][C:23]1[C:22]([O:32][CH3:33])=[C:21]([C:26]([O:27][CH3:28])=[CH:25][CH:24]=1)[C:20]([NH:19][C:3]1[C:2]([CH3:1])=[CH:7][C:6]([C:8]([F:17])([C:13]([F:14])([F:15])[F:16])[C:9]([F:12])([F:11])[F:10])=[CH:5][C:4]=1[CH3:18])=[O:34]

Participants

4

Reactant 1

HCID 59202377N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,6-dimethoxy-3-nitrobenzamide

Product 1

HCID 592023783-amino-N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,6-dimethoxy-benzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of N-[2,6-dimethyl-4-(1,2,2,2-tetrafluoro-1-trifluoromethyl-ethyl)-phenyl]-2,6-dimethoxy-3-nitrobenzamide (200 mg, 0.4 mmol) (see Example I3) in ethanol (8 ml) charged with Pd/C 10% (64 mg, 0.06 mmol) was stirred under a hydrogen atmosphere for 16 hours. After filtration the mixture was concentrated. The residue was used without further purification.

Workup

  1. filtrationAfter filtration the mixture
  2. concentrationwas concentrated
  3. customThe residue was used without further purification

Sources & evidence

ORD record
ord-b87f7f7f5a844755a3dfb2a52e95689b
Source dataset
uspto-grants-2013_04
Patent number
US08420855B2

Reaction notes

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