methyl 2-[(2-nitrophenyl)amino]benzoate → Methyl 2-(2-aminoanilino)benzoate

HRID 1747427Notes

Reaction equation

HRID 1747427 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[N+:17]([O-])=O>CCOC(C)=O.[Pd]>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH2:17]

Participants

4

Reactant 1

HCID 292094methyl 2-[(2-nitrophenyl)amino]benzoate

Product 1

HCID 13114778Methyl 2-(2-aminoanilino)benzoateYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-(2-Nitro-phenylamino)-benzoic acid methyl ester (200 mg, 0.74 mmol) is suspended in EtOAc (5.0 mL)) and 10% Pd/C wet (78 mg, 0.073 mmol) is added into it. A H2 balloon is attached to the reaction flask and the reaction mixture is stirred under H2 for 20 hrs. Then the Pd/C is filtered and the filtrated is concentrated to give 165 mg (93%) of 2-(2-Amino-phenylamino)-benzoic acid methyl ester.

Workup

  1. additionis added into it
  2. filtrationThen the Pd/C is filtered
  3. concentrationthe filtrated is concentrated

Sources & evidence

ORD record
ord-20e7940e4e344a9ba387c3c222c36f67
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…