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

HRID 54430Notes

Reaction equation

HRID 54430 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 Ci7H16F3NO: 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-8bcd73d971504e27bca95756cf957cb2
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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