Water → 1-(6-Acetyl-9H-carbazol-3-yl)-ethanone

HRID 514749

反応式

HRID 514749 の反応式
[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[C:18](Cl)([CH3:20])=[O:19].[OH2:22].[N+]([C:26]1[CH:31]=CC=CC=1)([O-])=O>>[C:18]([C:3]1[CH:2]=[CH:1][C:13]2[NH:12][C:11]3[C:6]([C:5]=2[CH:4]=1)=[CH:7][C:8]([C:31](=[O:22])[CH3:26])=[CH:9][CH:10]=3)(=[O:19])[CH3:20]

参加物

6

反応物 5

HCID 962WaterHCID 6367Acetyl chlorideHCID 6854CarbazoleHCID 7416NitrobenzeneHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 2364861-(6-Acetyl-9H-carbazol-3-yl)-ethanone収率 50%

実験手順

Carbazole 1 (16.9 g, 0.1 mol) was dissolved in nitrobenzene (300 mL). Anhydrous AlCl3 (54.0 g, 0.4 mol) was added under stirring and cooling with an ice bath. Then, AcCl (55.5 g, 0.7 mol) was added slowly dropwise. The reaction mixture was allowed to warm to room temperature under stirring and kept over a period of 13 h. Water (500 mL) was added in small portions under cooling with an ice bath. The cooling bath was removed, and the mixture was refluxed over a period of 2 h and extracted with CHCl3 (3×150 mL). The combined extracts were sequentially washed with saturated solutions of NaHCO3 and NaCl, dried with anhydrous Na2SO4, and evaporated. The residue was purified by column chromatography (silica gel, CHCl3/MeOH) to give 12.5 g (50%) of 3,6-diacetylcarbazole (4).

後処理

  1. temperaturecooling with an ice bath
  2. stirringunder stirring
  3. temperatureunder cooling with an ice bath
  4. customThe cooling bath was removed
  5. temperaturethe mixture was refluxed over a period of 2 h
  6. extractionextracted with CHCl3 (3×150 mL)
  7. washThe combined extracts were sequentially washed with saturated solutions of NaHCO3 and NaCl
  8. dry with materialdried with anhydrous Na2SO4
  9. customevaporated
  10. customThe residue was purified by column chromatography (silica gel, CHCl3/MeOH)

出典と根拠

ORDレコード
ord-0d18bcaceadb482e9e61c08fa4e9f8b7
出典データセット
uspto-grants-2015_08
特許番号
US09108916B2

関連ノート

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