HCID 68686617, compound → HCID 21957871, compound

HRID 1994065Notes

Reaction equation

HRID 1994065 reaction equation
[CH3:1][CH:2]([CH3:18])[CH:3]=[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-])=O)[C:5]([F:8])([F:7])[F:6]>CO.[Ni]>[CH3:1][CH:2]([CH3:18])[CH2:3][CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH2:15])[C:5]([F:6])([F:7])[F:8]

Participants

4

Reactant 1

HCID 68686617HCID 68686617, compound

Product 1

HCID 21957871HCID 21957871, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of 2.98 g (12.9 mmol) 1-(3-methyl-1-trifluoromethyl-but-1-enyl)-2-nitrobenzene in 30 ml methanol is hydrogenated over Raney-Nickel (ethanol) at 100° C. and 150 bar for 10 hours. Then the catalyst is filtered off and the solvent removed in a water-jet vacuum. The obtained crude product is purified by column chromatography over silica gel (eluant:hexane/methylene chloride=1:2). Yield: 1.9 g 2-(3-methyl-1-trifluoromethylbutyl)phenylamine in the form of a brown oil (1H-NMR).

Workup

  1. filtrationThen the catalyst is filtered off
  2. customthe solvent removed in a water-jet vacuum
  3. customThe obtained crude product
  4. customis purified by column chromatography over silica gel (eluant:hexane/methylene chloride=1:2)

Sources & evidence

ORD record
ord-c8f186544b27401b86b06adddc07d25c
Source dataset
uspto-grants-2010_01
Patent number
US07652059B2

Reaction notes

Loading…