3,5-Dimethyl-4-nitro-I,2-(methylenedioxy)benzene → 2,6-Dimethyl-3,4-(methylenedioxy)aniline

HRID 1090631Notes

Reaction equation

HRID 1090631 reaction equation
[CH3:1][C:2]1[C:3]2[O:14][CH2:13][O:12][C:4]=2[CH:5]=[C:6]([CH3:11])[C:7]=1[N+:8]([O-])=O.[H][H]>[Pd].C(O)C>[CH3:1][C:2]1[C:3]2[O:14][CH2:13][O:12][C:4]=2[CH:5]=[C:6]([CH3:11])[C:7]=1[NH2:8]

Participants

5

Reactant 2

HCID 199138223,5-Dimethyl-4-nitro-I,2-(methylenedioxy)benzeneHCID 178418361HCID 178418361, compound

Product 1

HCID 199138202,6-Dimethyl-3,4-(methylenedioxy)anilineYield 68%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

3,5-Dimethyl-4-nitro-I,2-(methylenedioxy)benzene (5.0 g) and 10% palladium on charcoal catalyst (1.2 g) in ethanol (250 ml) was shaken in a hydrogen atmosphere (50 p.s.i.) at 40° C. for 4 hours. The mixture was filtered through celite and evaporated to leave 2,6-dimethyl-3,4-(methylenedioxy)aniline (2.8 g, 68%) as a dark oil.

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-7f37fbeb302c400d979062df539b2ab5
Source dataset
uspto-grants-1992_01
Patent number
US05082848

Reaction notes

Loading…