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

HRID 54442Notes

Reaction equation

HRID 54442 reaction equation
C([C:5]([C:16]([C:18]([C:29](C)(C)C)=[CH:19]C1C=CC=C([N+]([O-])=O)C=1)=O)=[CH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[CH:8]=1)(C)(C)C.[C:33]1(=[O:40])[CH2:38][CH2:37][CH2:36][C:35](=O)[CH2:34]1.[C:41]([O-])(=O)C.[NH4+:45]>C(O)C>[C:18]([C:16]1[NH:45][C:37]2[CH2:36][CH2:35][CH2:34][C:33](=[O:40])[C:38]=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)([CH3:19])([CH3:29])[CH3:41]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 517165Ammonium AcetateHCID 86749015t-Butyl-3-nitrostyrylketone

Product 1

HCID 199589352-(t-Butyl)-4-(3-nitrophenyl)-4,6,7,8-tetrahydro-5(1H)-quinolone

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

t-Butyl-3-nitrostyrylketone (1.81 g), 1.3-cyclohexanedione (0.82 g), and ammonium acetate (1.25 g) were combined in ethanol (50 mL) and heated at reflux for 7.5 hours. Following removal of solvent and chromatography (hexane/ethyl acetate; 1:1 and methylene chloride/acetonitrile 9:1) the title compound (0.54 g) was obtained as a yellow solid; mp 180°-181.5° C.; NMR: 1.12 (s,9, CH3), 1.68-1.95 (m,2, CH2), 2.06-2.27 (m,2, CH2), 2.42-2.67 (m,2, CH2), 4.61 (d,1, J=5.2 CH), 4.72 (dd,1, J=5.2, 1.8; CH), 7.53 (m,1, Ar), 7.64 (m,1, Ar), 7.97 (m,2, Ar), 8.10 (s,1, NH); MS: m/z=326(M). Analysis for C19H22N2O3: Calculated: C, 69.92; H, 6.79; N, 8.58; Found: C, 69.96; H, 6.80; N, 8.60.

Workup

  1. temperatureheated
  2. temperatureat reflux for 7.5 hours
  3. customremoval of solvent and chromatography (hexane/ethyl acetate; 1:1 and methylene chloride/acetonitrile 9:1) the title compound (0.54 g)
  4. customwas obtained as a yellow solid

Sources & evidence

ORD record
ord-6aa5b87dbf6c47849a4f3b0092144406
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

Loading…