Acetamide, N-(2,4-dimethyl-5-nitrophenyl)- → Acetamide, N-(5-amino-2,4-dimethylphenyl)-

HRID 1702117

Reaction equation

HRID 1702117 reaction equation
[CH3:1][C:2]1[C:7]([NH:8][C:9]([CH3:11])=[O:10])=[CH:6][C:5]([N+:12]([O-])=O)=[C:4]([CH3:15])[CH:3]=1.[H][H].[S]>C(O)C.[Ni]>[CH3:15][C:4]1[C:5]([NH2:12])=[CH:6][C:7]([NH:8][C:9]([CH3:11])=[O:10])=[C:2]([CH3:1])[CH:3]=1

Participants

6

Reactant 3

HCID 112848Acetamide, N-(2,4-dimethyl-5-nitrophenyl)-HCID 5362487SulfurHCID 178418361HCID 178418361, compound2×

Product 1

HCID 104605Acetamide, N-(5-amino-2,4-dimethylphenyl)-

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

2,4-Dimethyl-5-nitroacetanilide (20.8 g., 100 mmole) in ethanol (400 ml.) was reduced over Raney nickel at about 45 psi of hydrogen gas. After the hydrogen uptake was complete, the mixture was deactivated with elementary sulfur, filtered, and the filtrate was evaporated under reduced pressure to give the product as a solid, m.p. 163°-164° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-df332bd22928459b9d6d0a925c87e2e5
Source dataset
uspto-grants-1983_04
Patent number
US04380464

Linked notes

Loading…