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

HRID 2209529Notes

Reaction equation

HRID 2209529 reaction equation
[CH3:1][CH:2]([CH3:17])[CH2:3][C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1.[C:18]1(=[O:25])[CH2:23][CH2:22][CH2:21][C:20](=O)[CH2:19]1.C([O-])(=O)C.[NH4+:30]>C(O)C>[CH2:3]([C:4]1[NH:30][C:20]2[CH2:21][CH2:22][CH2:23][C:18](=[O:25])[C:19]=2[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=2)[CH:5]=1)[CH:2]([CH3:17])[CH3:1]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 517165Ammonium AcetateHCID 542825645-Methyl-1-(3-nitrophenyl)-1-hexen-3-one

Product 1

HCID 199589152-(Isobutyl)-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)quinoloneYield 42.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-methyl-1-(3-nitrophenyl)-1-hexen-3-one (2.52 g), 1,3-cyclohexanedione (1.22 g) and ammonium acetate (1.88 g) in ethanol (65 mL) was stirred at reflux for 7.5 hours. After removal of the solvent, the residue was chromatographed (ethyl acetate/hexane 2:1) to yield the title compound (1.51 g) as a yellow solid; mp 158°-160° C.; NMR: 0.81 (d,3, J=5.8, CH3), 0.86 (d,3, J=5.8, CH3), 1.77-1.97 (m,5, CH2, CH), 2.10-2.23 (m,2, CH2), 2.46 (m,2, CH2), 4.59(d,1,J=4.8, CH), 4.64 (d,1, J=5.8, CH), 7.53 (m,1, Ar), 7.65 (m,1, Ar), 7.97 (m,2, Ar), 8.49 (s,1, NH); MS: m/z=326(M). Analysis for C19H22N 2 O3 : Calculated C, 69.92; H, 6.79; N, 8.58; Found: C, 70.03; H, 6.81; N, 8.54.

Workup

  1. temperatureat reflux for 7.5 hours
  2. customAfter removal of the solvent
  3. customthe residue was chromatographed (ethyl acetate/hexane 2:1)

Sources & evidence

ORD record
ord-95ed426344c7490e902a728128cc128b
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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