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

HRID 2209513Notes

Reaction equation

HRID 2209513 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-b28b017ded5c45a6b3c01cebf848c232
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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