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

HRID 54444Notes

Reaction equation

HRID 54444 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11](=O)[CH3:12])[CH:6]=[CH:7][CH:8]=1.[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>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([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:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 1820074-(3-Methoxyphenyl)but-3-en-2-oneHCID 517165Ammonium Acetate

Product 1

HCID 193812364-(3-Methoxyphenyl)-2-methyl-4,6,7,8-tetrahydro-5(1H)-quinoloneYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 1-(3-methoxyphenyl)but-1-en-3-one (2.07 g), 1,3-cyclohexanedione (1.37 g) and ammonium acetate (1.39 g) in ethanol (20 mL) was stirred at reflux for 10 hours. The reaction was worked up as described in Example 8 and purified by chromatography (10% v/v ethyl ether in methylene chloride) to yield the title compound (1.14 g) as an off-white solid. Recrystallization from ethanol/hexane gave analytically pure material, mp 164°-167° C.; NMR: 1.71 (s,3, CH3), 1.82-1.88 (m,2, CH2), 2.13-2.17 (m,2, CH2), 2.40-2.44 (m,2, CH2) 3.67 (s,3, CH3), 4.35 (d,1, J=4.8, CH), 4.60 (d,1, J=4.6, CH), 6.64-6.66 (m,2, Ar), 6.71 (d,1, J=7.7, Ar), 7.12 (dd,1, J=7.7, 3.8, Ar), 8.41 (s,1, NH); (CI, CH4)MS: m/z=270(M+1). Analysis for C17H19NO2.0.5H2O: Calculated: C, 73.36; H, 7.24; N, 5.03. Found: C, 73.49; H, 6.98; N, 4.93.

Workup

  1. temperatureat reflux for 10 hours
  2. custompurified by chromatography (10% v/v ethyl ether in methylene chloride)

Sources & evidence

ORD record
ord-448c584ce313458cbad5581b15ee93f2
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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