2-chloro-N,N-dimethyl-3-nitro-aniline → 2-Chloro-3-dimethylaminoaniline

HRID 394578Notes

Reaction equation

HRID 394578 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([N+:9]([O-])=O)[C:4]=1[Cl:12].[H][H]>CO.[Ni]>[Cl:12][C:4]1[C:3]([N:2]([CH3:13])[CH3:1])=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:9]

Participants

5

Reactant 2

HCID 227123482-chloro-N,N-dimethyl-3-nitro-anilineHCID 178418361HCID 178418361, compound

Product 1

HCID 227123462-Chloro-3-dimethylaminoanilineYield 49.5%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

30.4 g of N,N-dimethyl-2-chloro-3-nitroaniline is dissolved in about 300 ml of MeOH and hydrogenated at 20° C. and 5 bars pressure of hydrogen using Raney nickel as catalyst. The solvent is evaporated down and the product is purified by chromatography (silica gel, eluant: petroleum ether/ethyl acetate (3/1)). 12.8 g of 2-chloro-3-dimethylaminoaniline is obtained as a brown oil.

Workup

  1. customThe solvent is evaporated down
  2. customthe product is purified by chromatography (silica gel, eluant: petroleum ether/ethyl acetate (3/1))

Sources & evidence

ORD record
ord-5bd183b5c80e4da6ac9edaadda7ea8b9
Source dataset
uspto-grants-2003_08
Patent number
US06602897B2

Reaction notes

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