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

HRID 54440Notes

Reaction equation

HRID 54440 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10](=O)[CH3:11])[CH:5]=[CH:6][CH:7]=1.[CH3:13][C:14]1([CH3:22])[CH2:19][C:18](=O)[CH2:17][C:16](=[O:21])[CH2:15]1.C([O-])(=O)C.[NH4+:27]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:17]3[C:16](=[O:21])[CH2:15][C:14]([CH3:13])([CH3:22])[CH2:19][C:18]=3[NH:27][C:10]([CH3:11])=[CH:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 31358DimedoneHCID 1415763-ChlorobenzylideneacetoneHCID 517165Ammonium Acetate

Product 1

HCID 199589074-(3-Chlorophenyl)-2,7,7-trimethyl-4,6,7,8-tetrahydro-5(1H)quinoloneYield 56.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-(3-chlorophenyl)but-3-en-2-one (5.0 g), 5,5-dimethyl-1,3-cyclohexanedione (3.88 g), ammonium acetate (3.20 g) and ethanol (90 mL) was heated at reflux for ten hours. The reaction mixture was worked up as described in Example 8 and recrystallization from ethyl acetate-hexane yielded the title compound (4.7 g) as a light yellow solid, mp 183°-185° C.; NMR: 0.94(s,3, CH3), 1.00 (s,3, CH3), 1.74 (s,3, CH3), 1.95 (d,1, J=16, CH), 2.11 (d,1, J=16, CH), 2.25 (d,1, J=16.7, CH), 2.35 (d,1, J=16.7, CH), 4.38 (d,1, J=4.6, CH), 4.59 (d,1, J=4.6, CH), 7.09-7.28 (m,4, Ar), 8.44 (s,1, NH); (CI, CH4) MS: m/z=302(M+1). Analysis for C18H20ClNO: Calculated: C, 71.63; H, 6.68; N, 4.64; Found: C, 71.60; H, 6.69; N, 4.54.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for ten hours
  3. customas described in Example 8 and recrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c51cc104e9214f3d9bd0dbae42b5344e
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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