alpha-Ethyl-beta-oxobenzenepropanoic acid → 1-Benzoyl-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one

HRID 1637251ノート

反応式

HRID 1637251 の反応式
Cl.C1(NN)C=CC=CC=1.[C:10]1([C:16]2[NH:17][C:18]3[C:23]([C:24]=2[CH2:25][CH2:26][C:27](O)=[O:28])=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:30](C(CC)C(O)=O)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1>C(O)(=O)C>[C:30]([N:17]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]3[C:27](=[O:28])[CH2:26][CH2:25][CH:24]([C:23]=23)[CH:16]1[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

参加物

4

反応物 2

HCID 21651867alpha-Ethyl-beta-oxobenzenepropanoic acidHCID 703070592-phenylindole-3-propionic acid Phenylhydrazine hydrochloride

生成物 1

HCID 193483011-Benzoyl-2-phenyl-1,2,2a,3,4,5-hexahydrobenz[cd]indol-5-one収率 160.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

(Step 1) Synthesis of 2-phenylindole-3-propionic acid Phenylhydrazine hydrochloride (50 g) and benzoylbutyric acid (55.4 g) were suspended in acetic acid (500 ml), followed by heating to reflux for 1.5 hours. After allowing the suspension to cool, the insoluble matter was filtered off and the filtrate was concentrated under reduced pressure. Water was added to the residue, the mixture was extracted with ethyl acetate, and the organic layer was washed with water and saturated aqueous solution of sodium chloride, and thereafter dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was crystallized from an ether/hexane mixed solvent, followed by washing with a methylene chloride/hexane mixed solvent to yield 69 g (90%) of the titled compound as pale brown crystals.

後処理

  1. temperatureby heating
  2. temperatureto reflux for 1.5 hours
  3. temperatureto cool
  4. filtrationthe insoluble matter was filtered off
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. additionWater was added to the residue
  7. extractionthe mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with water and saturated aqueous solution of sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. customthe residue was crystallized from an ether/hexane mixed solvent
  12. washby washing with a methylene chloride/hexane mixed solvent

出典と根拠

ORDレコード
ord-18e26b6b07b9483a83da1ce235858637
出典データセット
uspto-grants-2000_03
特許番号
US06040331

反応ノート

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