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

HRID 2209526Notes

Reaction equation

HRID 2209526 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11](=O)[CH3:12])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:14]1(=[O:21])[CH2:19][CH2:18][CH2:17][C:16](=O)[CH2:15]1.C([O-])(=O)C.[NH4+:26]>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]2[C:15]3[C:14](=[O:21])[CH2:19][CH2:18][CH2:17][C:16]=3[NH:26][C:11]([CH3:12])=[CH:10]2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 3265634-(3,4-Dichlorophenyl)-3-buten-2-oneHCID 517165Ammonium Acetate

Product 1

HCID 199589084-(3,4-Dichlorophenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinoloneYield 36.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3,4-dichlorophenyl)but-1-en-3-one (5.0 g), 1,3-cyclohexanedione (2.71 g), ammonium acetate (2.70 g) and ethanol (75 mL) was heated at reflux for ten hours. The reaction was worked up as described in Example 8, and recrystallization from ethyl acetate-hexane yielded the title compound (2.6 g) as an off-white solid, mp 199°-201° C.; NMR: 1.74 (s,3, CH3), 1.84-1.88 (m,2, CH2), 2.14-2.19 (m,2, CH2), 2.41-2.46 (m,2, CH2), 4.42 (d,1, J=4.7, CH), 4.59 (d,1, J=4.7, CH), 7.12 (dd,1, J=8.3,2.0, Ar), 7.31 (d,1, J=2.0, Ar), 7.48 (d,1, J=8.3, Ar), 8.55 (s,1, NH); (CI, CH4) MS: m/z=308(M+1). Analysis for C16H15Cl2NO: Calculated C, 62.35; H, 4.91; N, 4.54; Found: C, 62.03; H, 5.09; N, 4.44.

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-b0acd04057484f908f00221d3c355e8c
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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