N,5-Dimethyl-2-nitroaniline → N1,5-Dimethylbenzene-1,2-diamine

HRID 1110815Notes

Reaction equation

HRID 1110815 reaction equation
[CH3:1][NH:2][C:3]1[CH:4]=[C:5]([CH3:12])[CH:6]=[CH:7][C:8]=1[N+:9]([O-])=O>CO.[C].[Pd]>[NH2:9][C:8]1[CH:7]=[CH:6][C:5]([CH3:12])=[CH:4][C:3]=1[NH:2][CH3:1]

Participants

4

Reactant 1

HCID 10103510N,5-Dimethyl-2-nitroaniline

Product 1

HCID 9989323N1,5-Dimethylbenzene-1,2-diamineYield 101.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

3-(N-Methylamino)-4-nitrotoluene (7.95 g) was catalytically reduced in a solution in 200 ml of methanol using 1.0 g of 10% palladium carbon as a catalyst. After the catalyst was filtered off, the reaction solution was concentrated under reduced pressure to give 6.60 g (101%) of 1-amino-4-methyl-2-(N-methylamino)benzene.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bef91445e3564d27a2a924c44cd70e50
Source dataset
uspto-grants-1990_12
Patent number
US04977175

Reaction notes

Loading…