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

HRID 2209510Notes

Reaction equation

HRID 2209510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]=[CH:9][C:10](=O)[CH3:11])=[CH:4][CH:3]=1.[C:13]1(=[O:20])[CH2:18][CH2:17][CH2:16][C:15](=O)[CH2:14]1.C([O-])(=O)C.[NH4+:25]>C(O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[C:14]3[C:13](=[O:20])[CH2:18][CH2:17][CH2:16][C:15]=3[NH:25][C:10]([CH3:11])=[CH:9]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

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

Product 1

HCID 199589244-(4-Chlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinoloneYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-(4-Chlorophenyl)-3-butene-2-one (2.83 g), 1.3-cyclohexanedione (1.81 g), and ammonium acetate (2.60 g) were combined in ethanol (125 mL) and heated at reflux for 5.5 h. The solvent was evaporated, and the residue was taken up in water and extracted with ethyl acetate. The combined organic extracts were washed (water, brine), dried, and evaporated to yield a residue which was chromatographed, eluting with hexane:ethyl acetate (1:1) to yield the title compound as a pale yellow solid (1.46 g); mp 184°-187° C.; MS: 273 (M); NMR: 1.73 (s,3, CH3), 1.75-1.98 (m,2, CH2), 2.15 (m,2, CH2), 2.43 (t,2, J=6.0, CH2), 4.39 (d,1, J=4.7, CH), 4.58 (d,1,J=4.8, CH), 7.14 (d,2, J=8.4, Ar), 7.26 (d,2, J=8.4, Ar), 8.48 (s,1, NH); Analysis for C16H16ClNO: Calculated C, 70.20; H, 5.89; N, 5.12; Found: C, 70.21; H, 5.67; N, 5.02.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5.5 h
  3. customThe solvent was evaporated
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed (water, brine)
  6. customdried
  7. customevaporated
  8. customto yield a residue which
  9. customwas chromatographed
  10. washeluting with hexane:ethyl acetate (1:1)

Sources & evidence

ORD record
ord-e1e80a3b9f554746a65500f224e316f7
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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