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

HRID 54436Notes

Reaction equation

HRID 54436 reaction equation
[CH3:1][CH:2]([CH3:14])[CH2:3][C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:15]1(=[O:22])[CH2:20][CH2:19][CH2:18][C:17](=O)[CH2:16]1.C([O-])(=O)C.[NH4+:27]>C(O)C>[CH2:3]([C:4]1[NH:27][C:17]2[CH2:18][CH2:19][CH2:20][C:15](=[O:22])[C:16]=2[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:5]=1)[CH:2]([CH3:14])[CH3:1]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 954715-Methyl-1-phenyl-hex-1-en-3-oneHCID 517165Ammonium Acetate

Product 1

HCID 199589062-Isobutyl-4-phenyl-4,6,7,8-tetrahydro-5(1H)-quinoloneYield 19.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5-Methyl-1-phenyl-1-hexen-3-one (5.05 g), 1,3-cyclohexanedione (3.31 g) and ammonium acetate (4.91 g) were combined in 200 mL of ethanol and allowed to reflux for 7 hours. The mixture was evaporated and the residue was purified by chromatography, with ethyl acetate as the eluent, to provide the title compound as a white solid (1.48 g); mp 182°-184° C.; MS: 281 (M); NMR: 0.79 (d,3, J=5.5, CH3), 0.85 (d,3, J=5.5, CH3), 1.73-1.93 (m,5, CH2, CH2, CH), 2.13 (m,2, CH2), 2.42 (m,2, CH2), 4.38 (d,1, J=4.9, CH), 4.58 (d,1, J=5.0, CH), 7.03-7.23 (m,5, Ar), 8.30 (s,1, NH). Analysis for C19H23NO: Calculated: C, 81.80; H, 8.24; N, 4.98; Found: C, 80.91; H, 8.21; N, 5.00.

Workup

  1. temperatureto reflux for 7 hours
  2. customThe mixture was evaporated
  3. customthe residue was purified by chromatography, with ethyl acetate as the eluent

Sources & evidence

ORD record
ord-fddc738e3f434ca1b5674eb8a831cb93
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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