[1-(2-Nitro-phenylamino)-cyclohexyl]-acetic acid methyl ester → [1-(2-Amino-phenylamino)-cyclohexyl]-acetic acid methyl ester

HRID 1747400Notes

Reaction equation

HRID 1747400 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-])=O)[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1>CCO.[Pd]>[CH3:1][O:2][C:3](=[O:21])[CH2:4][C:5]1([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[NH2:18])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

4

Reactant 1

HCID 59497614[1-(2-Nitro-phenylamino)-cyclohexyl]-acetic acid methyl ester

Product 1

HCID 59497703[1-(2-Amino-phenylamino)-cyclohexyl]-acetic acid methyl esterYield 99%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of [1-(2-nitro-phenylamino)-cyclohexyl]-acetic acid methyl ester (230 mg, 0.79 mmol), 10% Pd/C (80 mg) in EtOH (20 mL) under H2 atmosphere at room temperature was stirred for 16 h. The reaction mixture was filtered and the organic layer was concentrated to give the desired [1-(2-amino-phenylamino)-cyclohexyl]-acetic acid methyl ester (205 mg, 99%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe organic layer was concentrated

Sources & evidence

ORD record
ord-08d2d7a7e0fb4a5eb5b86790c3feb5a5
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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