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

HRID 719765

반응식

HRID 719765 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8f987316b9ed477d952fb3a0b5a4069b
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07132547B2

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