Vinyl Acetate → 1H-Indole, 1-benzoyl-

HRID 745314ノート

反応式

HRID 745314 の反応式
O[N:2]([C:9](=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:17](OC=C)(=O)[CH3:18]>>[C:9]([N:2]1[C:3]2[C:8](=[CH:7][CH:6]=[CH:5][CH:4]=2)[CH:18]=[CH:17]1)(=[O:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

参加物

3

反応物 2

HCID 7904Vinyl AcetateHCID 67536N-benzoyl-N-phenylhydroxylamine

生成物 1

HCID 2002831H-Indole, 1-benzoyl-

実験手順

8.3 g of N-hydroxybenzanilide are heated with 125 ml of vinyl acetate and 250 mg of Li2PdCl4 for four and a half hours at 60° C. The reaction mixture is washed with brine, dried over magnesium sulfate, and concentrated by evaporation. The solid residue is shaken with diethyl ether, in the process of which a small amount of crystalline benzanilide precipitates. The organic phase is concentrated by evaporation, and chromatographed through silica gel (toluene/diethyl ether 1:1). As the first fraction are obtained 6.2 g of N-benzoylindole, m.p. 54°-55° C.; IR spectrum (CHCl3): 1710 (CO): NMR spectrum (100 MHz, CDCl3) 6.52 (d, J=4, CH); 7.1-7.7 (m, 9H); 8.38 (m, 1H) ppm.

後処理

  1. washThe reaction mixture is washed with brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated by evaporation
  4. customprecipitates
  5. concentrationThe organic phase is concentrated by evaporation
  6. customchromatographed through silica gel (toluene/diethyl ether 1:1)

出典と根拠

ORDレコード
ord-52fec4362d084616bb7cafe1f8ab00f4
出典データセット
uspto-grants-1986_07
特許番号
US04598156

反応ノート

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