2-Cyclopentene-1,4-dione → 9-(3-bromo-4-fluorophenyl)-5,6,7,9-tetrahydro-1H-cyclopenta[b]quinoline-1,8(4H)-dione

HRID 1058679

반응식

HRID 1058679 반응식
[C:1]1(=[O:7])[CH:5]=[CH:4][C:3](=O)[CH2:2]1.[Br:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[F:17])[CH:12]=O.[NH2:18][C:19]1[CH2:24][CH2:23][CH2:22][C:21](=[O:25])[CH:20]=1>C(O)C>[Br:8][C:9]1[CH:10]=[C:11]([CH:12]2[C:20]3[C:21](=[O:25])[CH2:22][CH2:23][CH2:24][C:19]=3[NH:18][C:3]3[CH:4]=[CH:5][C:1](=[O:7])[C:2]2=3)[CH:14]=[CH:15][C:16]=1[F:17]

참가 물질

5

반응물 3

HCID 702582-Cyclopentene-1,4-dioneHCID 788923-Aminocyclohex-2-en-1-oneHCID 1736043-Bromo-4-fluorobenzaldehyde

생성물 1

HCID 97996939-(3-bromo-4-fluorophenyl)-5,6,7,9-tetrahydro-1H-cyclopenta[b]quinoline-1,8(4H)-dione

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A solution of 4-cyclopentene-1,3-dione (1.14 g, 10.2 mmol), 3-bromo-4-fluorobenzaldehyde (2.05 g, 10.1 mmol), and 3-amino-2-cyclohexenone (1.14 g, 10.2 mmol) in absolute ethanol (50 mL) were magnetically stirred and heated at reflux for 36 hours. The mixture was vacuum filtered and the solid was washed with ethyl acetate-hexane. The filtrate was concentrated and the residue was chromatographed on silica gel (100 g) using EtOAc-hexane (75:25), then EtOAc, finally EtOAc—EtOH (95:5). The product was obtained as a tan crystalline solid, (720 mg, 1.92 mmol).

후처리

  1. temperatureheated
  2. temperatureat reflux for 36 hours
  3. filtrationfiltered
  4. washthe solid was washed with ethyl acetate-hexane
  5. concentrationThe filtrate was concentrated
  6. customthe residue was chromatographed on silica gel (100 g)
  7. customThe product was obtained as a tan crystalline solid, (720 mg, 1.92 mmol)

출처 및 근거

ORD 기록
ord-ea5e65266bbd4132bb8757ab23bef667
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518279B2

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