2,3-Dimethyl-6-nitroaniline → 3,4-Dimethylbenzene-1,2-diamine

HRID 565207Notes

Reaction equation

HRID 565207 reaction equation
[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([N+:10]([O-])=O)[C:3]=1[NH2:4]>CO.[Ni]>[CH3:1][C:2]1[C:8]([CH3:9])=[CH:7][CH:6]=[C:5]([NH2:10])[C:3]=1[NH2:4]

Participants

4

Reactant 1

HCID 5971662,3-Dimethyl-6-nitroaniline

Product 1

HCID 5210773,4-Dimethylbenzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2,3-dimethyl-6-nitroaniline (83 g, 500 mmol) in methanol (1000 mL) was hydrogenated (H2, 50 psi) over Raney Nickel (5 g). On completion, the reaction mixture was filtered, and the mother liquor was evaporated to dryness to give a dark solid as the product.

Workup

  1. filtrationOn completion, the reaction mixture was filtered
  2. customthe mother liquor was evaporated to dryness
  3. customto give a dark solid as the product

Sources & evidence

ORD record
ord-79e7a1de399b4623b41e527d1e307704
Source dataset
uspto-grants-2001_01
Patent number
US06172065B2

Reaction notes

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