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

HRID 1258657Notes

Reaction equation

HRID 1258657 reaction equation
[Cl:1][C:2]1[C:8]([N:9]2[CH2:13][CH2:12][CH2:11][CH:10]2[CH2:14][N:15]([CH3:17])[CH3:16])=[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][CH2:11][CH:10]1[CH2:14][N:15]([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 679580054-Chloro-5-(2-dimethylaminomethyl-pyrrolidin-1-yl)-2-nitroaniline

Product 1

HCID 679577624-Chloro-5-(2-dimethylaminomethyl-pyrrolidin-1-yl)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-chloro-5-(2-dimethylaminomethyl-pyrrolidin-1-yl)-2-nitroaniline (150 mg, 0.5 mmol), EtOAc (10 mL) and Ra—Ni (50 mg) was stirred for 19 h at rt under a hydrogen atmosphere (3.0 bar). Further catalyst was added and the hydrogenation was continued for 6 h at 40° C. The catalyst was removed by filtration, the filtrate was acidified with 1.25 M HCl in EtOH and concentrated to give the sub-title compound.

Workup

  1. additionFurther catalyst was added
  2. waitthe hydrogenation was continued for 6 h at 40° C
  3. customThe catalyst was removed by filtration
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-082b39a2d8ff448f96ad8713e54cc2c6
Source dataset
uspto-grants-2013_06
Patent number
US08466186B2

Reaction notes

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