Ethanol → 2-Methyl-4-(4-methylphenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

HRID 2209514

Reaction equation

HRID 2209514 reaction equation
[CH3:1][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>CCOCC.CCCCCC.C(OCC)(=O)C>[CH3:11][C:10]1[NH:25][C:15]2[CH2:16][CH2:17][CH2:18][C:13](=[O:20])[C:14]=2[CH:8]([C:5]2[CH:6]=[CH:7][C:2]([CH3:1])=[CH:3][CH:4]=2)[CH:9]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 104341,3-CyclohexanedioneHCID 1073884-(4-Methylphenyl)-3-buten-2-oneHCID 517165Ammonium Acetate

Product 1

HCID 199589302-Methyl-4-(4-methylphenyl)-4,6,7,8-tetrahydro-5(1H)-quinoloneYield 25.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

A mixture of 4-(4-methyphenyl)-3-butene-2-one (5.0 g), 1,3-cyclohexanedione (3.66 g), ammonium acetate (3.61 g) and 100 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 an amber oil. Chromatography, with hexane:ethyl acetate (1:1) as the eluent, and trituration from ether provided the title compound as an off-white solid (2.0 g); mp 196°-198° C.; NMR: 1.73 (s,3, CH3), 1.87-1.98 (m,2, CH2), 2.14-2.16 (m,2, CH2), 2.22 (s,3, CH3), 2.43-2.49 (m,2, CH2), 4.34 (d,1, CH), 4.57 (d,1, CH), 7.01 (s,4, Ar), 8.40 (s,1, NH); (CI, CH4) MS: m/z=254(M+1). Analysis for C17H19NO: Calculated C, 80.60; H, 7.56; N, 5.53; Found: C, 80.24; H, 7.68; N, 5.36.

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 an amber oil

Sources & evidence

ORD record
ord-98b6075338e347a99060ffceb9a3fdce
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Linked notes

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