2-(Difluoromethoxy)-6-nitrotoluene → 3-(Difluoromethoxy)-2-methylaniline

HRID 628491Notes

Reaction equation

HRID 628491 reaction equation
[F:1][CH:2]([F:14])[O:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[C:5]=1[CH3:13]>[C].[Pd].C(O)C>[F:1][CH:2]([F:14])[O:3][C:4]1[C:5]([CH3:13])=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH2:10]

Participants

4

Reactant 1

HCID 682816542-(Difluoromethoxy)-6-nitrotoluene

Product 1

HCID 434378993-(Difluoromethoxy)-2-methylanilineYield 100.1%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of the above-prepared 1-difluoromethoxy-2-methyl-3-nitrobenzene (described in Reference Preparation example 3) 7.50 g, palladium-carbon (palladium 5%) 0.8 g and ethanol 80 ml was stirred at room temperature under hydrogen atmosphere for eight hours. The reaction mixture was filtered and the filtrate was concentrated to give 3-difluoromethoxy-2-methylaniline 6.4 g.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-3499dfe115ea4c8e857bad23413c3625
Source dataset
uspto-grants-2016_04
Patent number
US09314023B2

Reaction notes

Loading…