N-(2-fluoro-5-nitrophenyl)benzamide → N-(5-Amino-2-fluorophenyl)benzamide

HRID 724432Notes

Reaction equation

HRID 724432 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12](=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>[Pd].C1COCC1.CO>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([NH:11][C:12](=[O:19])[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:4]=1

Participants

4

Reactant 1

HCID 675819N-(2-fluoro-5-nitrophenyl)benzamide

Product 1

HCID 11148928N-(5-Amino-2-fluorophenyl)benzamideYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A mixture of N-(2-fluoro-5-nitro-phenyl)-benzamide (4.86 g, 18.7 mmol) and 10% Pd/C (486 mg) in a 1:1 mixture of THF-MeOH (80 ml) was hydrogenated at 23° C. After 2.5 h the reaction mixture was filtered through celite and concentrated to give N-(5-Amino-2-fluoro-phenyl)-benzamide (3.92 g, 91%). MS (ESI+) [M+H]/z Calc'd 231. found 231.

Workup

  1. customwas hydrogenated at 23° C
  2. filtrationAfter 2.5 h the reaction mixture was filtered through celite and
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-4cf1559bac90484eb09770de2041e2c8
Source dataset
uspto-grants-2006_11
Patent number
US07141587B2

Reaction notes

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