[2-Nitro-3-(3-nitro-phenylamino)-phenyl]-acetic acid ethyl ester → [2-Amino-3-(3-amino-phenylamino)-phenyl]-acetic acid ethyl ester

HRID 422019Notes

Reaction equation

HRID 422019 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-])=O)[CH:14]=2)[C:7]=1[N+:22]([O-])=O)[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([NH2:19])[CH:14]=2)[C:7]=1[NH2:22])[CH3:2]

Participants

4

Reactant 1

HCID 59804286[2-Nitro-3-(3-nitro-phenylamino)-phenyl]-acetic acid ethyl ester

Product 1

HCID 59804307[2-Amino-3-(3-amino-phenylamino)-phenyl]-acetic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of [2-nitro-3-(3-nitro-phenylamino)-phenyl]-acetic acid ethyl ester (0.62 g, 1.8 mmol) in ethanol (50 ml) is added Pd/C (10%, wet, 0.50 g). It is placed under a hydrogen balloon and stirred for 20 hours. The catalyst is filtered and the solvent is removed to give the desired compound: LC-MS: 286.1 (MH+).

Workup

  1. filtrationThe catalyst is filtered
  2. customthe solvent is removed

Sources & evidence

ORD record
ord-d525e89864114f1f89bf883ef3009cc7
Source dataset
uspto-grants-2012_01
Patent number
US08101608B2

Reaction notes

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