N-(2,2-difluoroethyl)-2-nitroaniline → N-(2,2-difiuoroethyl)benzene-1,2-diamine

HRID 76359

Reaction equation

HRID 76359 reaction equation
[F:1][CH:2]([F:14])[CH2:3][NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-])=O>CO.[Pd]>[F:1][CH:2]([F:14])[CH2:3][NH:4][C:5]1[C:6]([NH2:11])=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

4

Reactant 1

HCID 58110950N-(2,2-difluoroethyl)-2-nitroaniline

Product 1

HCID 58110951N-(2,2-difiuoroethyl)benzene-1,2-diamineYield 97.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3.6 g (18 mM) of N-(2,2-difluoroethyl)-2-nitroaniline in 25 ml of methanol, were added 470 mg of palladium on carbon at 5%. The reaction mixture was stirred for 3 h at room temperature under hydrogen atmosphere, at room pressure and room temperature. The catalyst was filtrated on Celite and the filtrate was evaporated under vacuum to give 3 g of N-(2,2-difluoroethyl)benzene-1,2-diamine as an oil. Yield: 97.5%.

Workup

  1. filtrationThe catalyst was filtrated on Celite
  2. customthe filtrate was evaporated under vacuum

Sources & evidence

ORD record
ord-822ae9bbc4524223ac08e97fa7569401
Source dataset
uspto-grants-2014_09
Patent number
US08835634B2

Linked notes

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