Ethanol → 4-(3-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 54431

Reaction equation

HRID 54431 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](C=CC(=O)C)=[CH:4][CH:3]=1.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.[C:21]([O-])(=O)[CH3:22].[NH4+:25].[CH2:26](O)[CH3:27]>>[Cl:1][C:2]1[CH:7]=[C:6]([CH:26]2[C:14]3[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=3[NH:25][C:21]([CH3:22])=[CH:27]2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 104341,3-CyclohexanedioneHCID 981834-ChlorobenzalacetoneHCID 517165Ammonium Acetate

Product 1

HCID 199589214-(3-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinolone

Procedure

A mixture of 4-(4-chlorophenyl)-3-butene-2-one (5.0 g), 1,3-cyclohexanedione (3.24 g), ammonium acetate (3.20 g) and 90 mL of ethanol were heated at reflux overnight and then cooled to room temperature. The solvent was evaporated and the residue was partitioned between water and ethyl acetate. The organic layer was dried, filtered, and evaporated to obtain a yellow solid. Recrystallization from ethanol provided the title compound as a yellow solid (3.0 g); mp 201°-203° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.13-2.17 (m,2, CH2), 2.43-2.49 (m,2, CH2), 4.40 (d,1, J=4.9, CH), 4.60 (d,1, J=4.9, CH), 7.09-7.25 (m,4, Ar), 8.50 (s,1, NH); (CI, CH4) MS: m/z=274(M+1). Analysis for C16H16ClNO.0.15 H2O: Calculated: C, 69.51; H, 5.94; N, 5.07; Found: C, 69.47; H, 6.03; N, 4.91.

Workup

  1. temperaturewere heated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated
  4. customthe residue was partitioned between water and ethyl acetate
  5. customThe organic layer was dried
  6. filtrationfiltered
  7. customevaporated
  8. customto obtain a yellow solid
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-fb6dfcb9be9c41c0b751a04f63012648
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Linked notes

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