HCID 68686617, compound → HCID 68683965, compound

HRID 1994064Notes

Reaction equation

HRID 1994064 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.[Pd]>[CH3:1][CH:2]([CH3:18])[CH:3]=[C: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 68683965HCID 68683965, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 1.14 g (4.4 mmol) 1-(3-methyl-1-trifluoromethyl-but-1-enyl)-2-nitrobenzene in 20 ml methanol is hydrogenated over 10% Pd/C (230 mg) at room temperature for 20 minutes. Then the catalyst is filtered off and the solvent removed in a water-jet vacuum. The crude product is purified by column chromatography over silica gel (eluant:methylenechloride/hexane=2:1). Yield: 0.6 g ((sum E+Z isomer) 2-(3-methyl-1-trifluoromethyl-but-1-enyl)phenylamine in the form of a brown oil. After column chromatography both isomers are obtained in pure form (1H-NMR).

Workup

  1. filtrationThen the catalyst is filtered off
  2. customthe solvent removed in a water-jet vacuum
  3. customThe crude product is purified by column chromatography over silica gel (eluant:methylenechloride/hexane=2:1)
  4. customAfter column chromatography both isomers are obtained in pure form (1H-NMR)

Sources & evidence

ORD record
ord-cda66103c8f04ed6aa4615f6dc47e9ba
Source dataset
uspto-grants-2010_01
Patent number
US07652059B2

Reaction notes

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