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

HRID 1292395ノート

反応式

HRID 1292395 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-3b90f590687e4e068ae06cc3c3fd3d13
出典データセット
uspto-grants-1998_05
特許番号
US05756507

反応ノート

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