3-Fluoro-N,N-dimethyl-4-nitrobenzamide → 4-Amino-3-fluoro-N,N-dimethylbenzamide

HRID 2217484Notes

Reaction equation

HRID 2217484 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[N+:13]([O-])=O)[C:5]([N:7]([CH3:9])[CH3:8])=[O:6]>[Ni].C1COCC1>[NH2:13][C:12]1[CH:11]=[CH:10][C:4]([C:5]([N:7]([CH3:9])[CH3:8])=[O:6])=[CH:3][C:2]=1[F:1]

Participants

4

Reactant 1

HCID 221815783-Fluoro-N,N-dimethyl-4-nitrobenzamide

Product 1

HCID 221815204-Amino-3-fluoro-N,N-dimethylbenzamideYield 100%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a Parr apparatus was added 4 (0.78 g, 3.67 mmol), Raney nickel (1.2 g), and THF (50 mL). The vessel was sealed under a hydrogen atmosphere and shaken under pressure at room temperature for 15 h. The vessel was then depressurized and the solids filtered off, washing with THF. The filtrate was concentrated under reduced pressure to give impure 5 (0.66 g, 100%). MS: APCI (AP+): 183.1 (M)+, (AP−): 181.0 (M)−.

Workup

  1. customThe vessel was sealed under a hydrogen atmosphere
  2. filtrationthe solids filtered off
  3. washwashing with THF
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-f8dc56cafe8349009c4e132e1d5da557
Source dataset
uspto-grants-2008_08
Patent number
US07407972B2

Reaction notes

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