4-(Benzoyloxy)cyclohexanone → 3-Benzoyloxy-6-cyano-1,2,3,4-tetrahydrocarbazole

HRID 53322ノート

反応式

HRID 53322 の反応式
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10]N)=[CH:6][CH:5]=1)#[N:3].[C:12]([O:20][CH:21]1[CH2:26][CH2:25][C:24](=O)[CH2:23][CH2:22]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)(=O)C>[C:12]([O:20][CH:21]1[CH2:22][C:23]2[C:8]3[C:7](=[CH:6][CH:5]=[C:4]([C:2]#[N:3])[CH:9]=3)[NH:10][C:24]=2[CH2:25][CH2:26]1)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

4

反応物 2

HCID 2426774-(Benzoyloxy)cyclohexanoneHCID 162129624-Cyanophenylhydrazine Hydrochloride

生成物 1

HCID 218436753-Benzoyloxy-6-cyano-1,2,3,4-tetrahydrocarbazole収率 47.9%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

4-Cyanophenyl hydrazine hydrochloride (20.2 g) and 4-benzoyloxycyclohexanone (25.9 g) were dissolved in glacial acetic acid (400 ml) and the mixture was heated under reflux for 1.5 hr. After allowing to cool, the mixture was filtered, and the filtrate was evaporated to dryness, and neutralized with aqueous sodium bicarbonate solution to give a solid precipitate, which was purified by chromatography (SiO2 ; hexane/ethyl acetate) to give 3-benzoyloxy-6-cyano-1,2,3,4-tetrahydrocarbazole (18 g). This product (11.6 g) was suspended in ethanol (230 ml) and treated with 2.5% aqueous potassium hydroxide solution (120 ml), and heated under reflux for 1 hr. The cooled mixture was neutralized with glacial acetic acid and evaporated to a solid residue, which was washed with water, and dried to give 3-hydroxy-6-cyano-1,2,3,4-tetrahydrocarbazole (6.6 g).

後処理

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. temperatureto cool
  4. filtrationthe mixture was filtered
  5. customthe filtrate was evaporated to dryness
  6. customto give a solid precipitate, which
  7. customwas purified by chromatography (SiO2 ; hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-95c8536528094ff3a2cd816546f13da3
出典データセット
uspto-grants-1997_04
特許番号
US05618948

反応ノート

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