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

反応式

HRID 1058679 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ea5e65266bbd4132bb8757ab23bef667
出典データセット
uspto-grants-2003_02
特許番号
US06518279B2

関連ノート

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