2-Iodo-4-nitroaniline → 2-(3,5-Dimethylphenylethynyl)-4-nitrophenylamine

HRID 1292395Notes

Reaction equation

HRID 1292395 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]#[CH:10])[CH:5]=[C:6]([CH3:8])[CH:7]=1.I[C:12]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=1[NH2:14]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:1][C:2]1[CH:3]=[C:4]([C:9]#[C:10][C:12]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:13]=2[NH2:14])[CH:5]=[C:6]([CH3:8])[CH:7]=1

Participants

4

Reactant 2

HCID 2226292-Iodo-4-nitroanilineHCID 64326111-Ethynyl-3,5-dimethylbenzene

Product 1

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

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of 3,5-dimethylphenylethyne (156 mg in 7 mL of dry, nitrogen saturated triethylamine) was added 2-iodo-4-nitroaniline (264 mg, prepared essentially as described in: Toth, I. Helv. Chim. Acta, 1971, 54, 1486.) followed by tetrakis(triphenylphosphine)palladium (23 mg) and cuprous bromide (10 mg) and the mixture heated to reflux on an oil bath. After 2 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 give the title compound (256 mg).

Workup

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

Sources & evidence

ORD record
ord-3b90f590687e4e068ae06cc3c3fd3d13
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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