2-(3,5-Dimethylphenylethynyl)-4-nitrophenylamine → HCID 21254069, compound

HRID 1292396Notes

Reaction equation

HRID 1292396 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=2[NH2:20])[CH:5]=[C:6]([CH3:8])[CH:7]=1>[Pd](Cl)Cl>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:20][C:12]3[C:11]([CH:10]=2)=[CH:16][C:15]([N+:17]([O-:19])=[O:18])=[CH:14][CH:13]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

3

Reactant 1

HCID 189142732-(3,5-Dimethylphenylethynyl)-4-nitrophenylamine

Product 1

HCID 21254069HCID 21254069, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 24290Palladium ChlorideCatalyst

Procedure

To a stirred solution of 2-(3,5-dimethylphenylethynyl)-4-nitrophenylamine (50 mg in 3 mL of dry, nitrogen saturated acetonitrile) was added 5 mg of palladium (II) chloride and the mixture heated to reflux on an oil bath. After 3 hours the mixture was cooled to room temperature, concentrated in vacuo and purified by flash chromatography on silica gel (hexane:methylene chloride:ethyl acetate 15:8:1) to provide the title compound (46 mg).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux on an oil bath
  3. concentrationconcentrated in vacuo
  4. custompurified by flash chromatography on silica gel (hexane:methylene chloride:ethyl acetate 15:8:1)

Sources & evidence

ORD record
ord-926be2d9a99e4042bb6c4df38ee244ee
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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