1,3-Cyclohexanedione → HCID 19381235, compound

HRID 2209523Notes

Reaction equation

HRID 2209523 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12](=O)[CH2:13][CH3:14])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:16]1(=[O:23])[CH2:21][CH2:20][CH2:19][C:18](=O)[CH2:17]1.C([O-])(=O)C.[NH4+:28]>C(O)C>[CH2:13]([C:12]1[NH:28][C:18]2[CH2:19][CH2:20][CH2:21][C:16](=[O:23])[C:17]=2[CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[CH:11]=1)[CH3:14]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 517165Ammonium AcetateHCID 54402068HCID 54402068, compound

Product 1

HCID 19381235HCID 19381235, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-(3-nitrophenyl)-1-penten-3-one (2.42 g), 1,3-cyclohexanedione (1.36 g), ammonium acetate (2.00 g) and ethanol (70 mL) was heated at reflux for 7.5 hours. Removal of solvent, chromatography (ethyl acetate/hexane, 2:1 and methylene chloride/acetonitrile, 9:1), trituration with hot diethyl ether and recrystallization from ethyl acetate provided the title compound (1.29 g) as a yellow solid; mp 182°-184° C.; NMR: 1.03 (t,3, J=7.4, CH3), 1.70-1.95 (m,2, CH2), 2.07 (q,2, J=7.5, CH2), 2.17 (m,2, CH2), 2.48 (m,2, CH2), 4.59 (d,1, J=4.8, CH), 4.66 (dd, 1, J=4.8, 0.9, CH), 7.53 (m,1, Ar), 7.64 (m,1, Ar), 7.98 (m,2, Ar), 8.55 (s,1, NH). MS: m/z= 298(M). Analysis for C17H18N2O3 : Calculated: C., 68.44; H, 6.08; N, 9.39; Found: C, 68.43; H, 6.09; N, 9.39.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7.5 hours
  3. customRemoval of solvent, chromatography (ethyl acetate/hexane, 2:1 and methylene chloride/acetonitrile, 9:1), trituration
  4. customwith hot diethyl ether and recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-b4ed7aa1f21e40aa9a1a553beef566de
Source dataset
uspto-grants-1995_10
Patent number
US05455253

Reaction notes

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