1,3-Cyclohexanedione → 2-Methyl-4-(4-trifluoromethylphenyl)-4,6,7,8-tetrahydro-5(1h)-quinolone

HRID 2209512Notes

Reaction equation

HRID 2209512 reaction equation
[F:1][C:2]([F:15])([F:14])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11](=O)[CH3:12])=[CH:5][CH:4]=1.[C:16]1(=[O:23])[CH2:21][CH2:20][CH2:19][C:18](=O)[CH2:17]1.C([O-])(=O)C.[NH4+:28]>C(O)C>[CH3:12][C:11]1[NH:28][C:18]2[CH2:19][CH2:20][CH2:21][C:16](=[O:23])[C:17]=2[CH:9]([C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:15])([F:14])[F:1])=[CH:4][CH:5]=2)[CH:10]=1

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 1447744-[4-(Trifluoromethyl)phenyl]but-3-en-2-oneHCID 517165Ammonium Acetate

Product 1

HCID 199589002-Methyl-4-(4-trifluoromethylphenyl)-4,6,7,8-tetrahydro-5(1h)-quinoloneYield 56.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(4-trifluoromethyphenyl)-3-butene-2-one (4.9 g), 1,3-cyclohexanedione (2.68 g), ammonium acetate (2.65 g) and 75 mL of ethanol were heated at reflux for eight hours 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 oil. Chromatography, with hexane:ethyl acetate (1:1) as the eluent, and recrystallization from toluene:hexane provided the title compound as a yellow solid (4.0 g); mp 116°-118° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.14-2.16 (m,2, CH2), 2.45-2.49 (m,2, CH2), 4.49 (d,1, J=4.9, CH), 4.60 (d,1, J=4.9, CH), 7.35 (d,2, J=8.0, Ar), 7.57 (d,2, J=8.0, Ar), 8.54 (s,1, NH); (CI, CH4) MS: m/z=308(M+1); Analysis for C17H16F3NO: Calculated C, 66.44; H, 5.25; N, 4.56; Found: C, 66.72; H, 5.34; N, 4.41.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for eight hours
  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 oil
  9. customChromatography, with hexane:ethyl acetate (1:1) as the eluent, and recrystallization from toluene

Sources & evidence

ORD record
ord-6d70d869a84646cda50c3fa6737818e4
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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