N-(4-fluorophenyl)-2-nitrobenzamide → 2-amino-N-(4-fluorophenyl)benzamide

HRID 427602

Reaction equation

HRID 427602 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-])=O)=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.O1CCCC1.O.O.O.O.C([O-])(=O)C.[Ni+2].C([O-])(=O)C>[NH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)=[O:19]

Participants

6

Reactant 2

HCID 691037N-(4-fluorophenyl)-2-nitrobenzamideHCID 4311764Sodium borohydride

Product 1

HCID 4788222-amino-N-(4-fluorophenyl)benzamideYield 81%

Reagents, catalysts & solvents 3

HCID 62601Nickel acetate tetrahydrateCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of N-(4-fluorophenyl)-2-nitrobenzamide (4.0 g, 15.4 mmol) in methanol (220 mL) and tetrahydrofuran (110 mL) was added nickel acetate tetrahydrate (7.7 g, 31 mmol). Sodium borohydride (2.3 g, 62 mmol) was added in small portions. After gas evolution had ceased, the solvent was removed in vacuo. The residue was partitioned between ethyl acetate and concentrated ammonium hydroxide, and the layers were separated. The organic phase was washed with concentrated ammonium hydroxide and saturated aqueous sodium chloride solution, dried (magnesium sulfate), filtered, and concentrated in vacuo to give 2.86 g (81%) of the title compound as an off-white solid.

Workup

  1. customthe solvent was removed in vacuo
  2. customThe residue was partitioned between ethyl acetate and concentrated ammonium hydroxide
  3. customthe layers were separated
  4. washThe organic phase was washed with concentrated ammonium hydroxide and saturated aqueous sodium chloride solution
  5. dry with materialdried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4e3ffc13d5264bc4bc9ada48cfeaba5f
Source dataset
uspto-grants-2001_11
Patent number
US06313122B1

Linked notes

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