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

Reaction equation

HRID 1058679 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-ea5e65266bbd4132bb8757ab23bef667
Source dataset
uspto-grants-2003_02
Patent number
US06518279B2

Linked notes

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