Ethyl 4-[(2-nitrophenyl)amino]benzoate → Ethyl 4-[(2-aminophenyl)amino]benzoate

HRID 1921197Notes

Reaction equation

HRID 1921197 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1

Participants

4

Reactant 1

HCID 11208411Ethyl 4-[(2-nitrophenyl)amino]benzoate

Product 1

HCID 18449398Ethyl 4-[(2-aminophenyl)amino]benzoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 4-[(2-nitrophenyl)amino]benzoate from Step A (755 mg, 2.64 mmol) and 10% Pd/C (505 mg) in EtOH (25 mL) was stirred under an atmosphere of hydrogen (ca.1 atm) for 4 h. The mixture was filtered through a pad of Celite, washing with EtOH, and the filtrate was concentrated to give the title compound. MS: m/z=257 (M+1).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b159f1925a5943e69478c1325bba95e5
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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