2-Nitro-N-Phenylbenzamide → 2-Amino-N-phenylbenzamide

HRID 574103Notes

Reaction equation

HRID 574103 reaction equation
[N+:1]([C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7])([O-])=O.[B][B][B][B][B][B][B][B][B][B]>CO.[Pd]>[NH2:1][C:4]1[CH:18]=[CH:17][CH:16]=[CH:15][C:5]=1[C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:7]

Participants

5

Reactant 2

HCID 7200512-Nitro-N-PhenylbenzamideHCID 178419135HCID 178419135, compound

Product 1

HCID 781422-Amino-N-phenylbenzamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-nitro-N-phenylbenzamide (5 g; 20.7 mmol; 1 equiv.) in MeOH (65 mL) was added palladium on charcoal (550 mg) and decaborane (757 mg; 6.2 mmol; 0.3 equiv.) at room temperature. The mixture was heated at 60° C. for 6 hours, filtered over celite, washed with AcOEt and evaporated to give 2-amino-N-phenylbenzamide as brown solid (4.2 g; 96%) which was used without further purification.

Workup

  1. filtrationfiltered over celite
  2. washwashed with AcOEt
  3. customevaporated

Sources & evidence

ORD record
ord-359d6dbce5ed4d58bf37813371f09125
Source dataset
uspto-grants-2015_05
Patent number
US09034868B2

Reaction notes

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