4-Chloro-5-(3-dimethylaminomethyl-pyrrolidin-1-yl)-2-nitroaniline → 4-Chloro-5-(3-dimethylaminomethyl-pyrrolidin-1-yl)-benzene-1,2-diamine

HRID 1258638Notes

Reaction equation

HRID 1258638 reaction equation
[Cl:1][C:2]1[C:8]([N:9]2[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH3:17])[CH3:16])[CH2:10]2)=[CH:7][C:5]([NH2:6])=[C:4]([N+:18]([O-])=O)[CH:3]=1>[Ni].CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH2:18])[C:5]([NH2:6])=[CH:7][C:8]=1[N:9]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH3:16])[CH3:17])[CH2:10]1

Participants

4

Reactant 1

HCID 679579424-Chloro-5-(3-dimethylaminomethyl-pyrrolidin-1-yl)-2-nitroaniline

Product 1

HCID 679579304-Chloro-5-(3-dimethylaminomethyl-pyrrolidin-1-yl)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-5-(3-dimethylaminomethyl-pyrrolidin-1-yl)-2-nitroaniline (630 mg, 2.1 mmol), EtOAc (20 mL) and Ra—Ni (150 mg) was stirred for 2 days at rt under a hydrogen atmosphere (3.0 bar). The catalyst was removed by filtration and the filtrate was concentrated. The crude was purified by chromatography to give the sub-title compound.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-1adaa7f3ad76482bb3cf3a0f30e9933e
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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