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

HRID 128753

반응식

HRID 128753 반응식
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

참가 물질

4

반응물 2

HCID 2426774-(Benzoyloxy)cyclohexanoneHCID 162129624-Cyanophenylhydrazine Hydrochloride

생성물 1

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

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-3d6fe5828aed459da4f28a027da75528
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464864

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