5-Chlorovaleryl chloride → 8-(5-chloropentanoyl)-5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-4(2H)-one

HRID 719765

反応式

HRID 719765 の反応式
[Cl-].[Al+3].[Cl-].[Cl-].[CH2:5]1[C:15]2=[C:16]3[C:11](=[CH:12][CH:13]=[CH:14]2)[CH2:10][CH2:9][C:8](=[O:17])[N:7]3[CH2:6]1.[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](Cl)=[O:24]>ClCCCl>[Cl:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([C:13]1[CH:12]=[C:11]2[C:16]3=[C:15]([CH2:5][CH2:6][N:7]3[C:8](=[O:17])[CH2:9][CH2:10]2)[CH:14]=1)=[O:24]

参加物

5

反応物 3

HCID 740895-Chlorovaleryl chlorideHCID 91665PyroquilonHCID 6451240Aluminum(III) Chloride

生成物 1

HCID 111738438-(5-chloropentanoyl)-5,6-dihydro-1H-pyrrolo[3,2,1-ij]quinolin-4(2H)-one

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

Aluminum chloride (55 g, 410 mmol) was added by portions to a solution of 1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one (30.0 g) and 5-chlorovaleryl chloride (26.8 ml) in 1,2-dichloroethane (70 ml) under ice-cooling. After stirring at room temperature for 30 minutes, the reaction mixture was poured into ice (500 g), extracted with ethyl acetate, and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was recrystallized from ethanol-diethyl ether to give a pale yellow solid (36.5 g). Further recrystallization from ethanol-diethyl ether afforded the title compound as colorless crystals (32.4 g) having a melting point of 110–111° C.

後処理

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was recrystallized from ethanol-diethyl ether

出典と根拠

ORDレコード
ord-8f987316b9ed477d952fb3a0b5a4069b
出典データセット
uspto-grants-2006_11
特許番号
US07132547B2

関連ノート

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