1,3-Cyclohexanedione → HCID 19958936, compound

HRID 54433Notes

Reaction equation

HRID 54433 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]2=[O:17])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][C:20](=O)[CH2:19]1.C([O-])(=O)C.[NH4+:30]>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]2[C:11]3[C:12](=[O:17])[CH2:13][CH2:14][CH2:15][C:16]=3[NH:30][C:18]3[CH2:23][CH2:22][CH2:21][CH2:20][C:19]2=3)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 104341,3-CyclohexanedioneHCID 517165Ammonium AcetateHCID 537541182-(3-Nitrophenylmethylene)cyclohexanone

Product 1

HCID 19958936HCID 19958936, compoundYield 7.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-(3-nitrophenylmethylene)cyclohexanone (4.69 g), 1,3-cyclohexanedione (2.28 g), ammonium acetate (2.35 g) and 90 mL of ethanol was stirred at reflux under nitrogen for 48 hours. The mixture was cooled in an ice bath and orange crystals were collected by filtration. The material was chromatographed with dichloromethane, ethyl ether:dichloromethane (2:98) and ethyl ether:dichloromethane (10:90) as the elutents. The solvent was evaporated and the residue recrystallized from toluene/hexane to yield the title compound as yellow crystals (0.50 g); mp 218°-221° C.; NMR (CDCl3): 1.57-1.59 (m,4, CH2) 1.74-1.80 (m,2, CH2) 1.88-2.01 (m,2, CH2) 2.14 (broad s,2, CH2) 2.28-2.36 (m,2, CH2) 2.42-2.46 (m,2, CH2) 4.50 (s,1, CH) 5.40 (s,1, NH) 7.38 (t,1, J=7.8, Ar) 7.71 (d,1, J=7.6, Ar) 7.98 (q,1, J=7.3, 1.4, Ar) 8.09 (d,1, J=1.9, Ar); MS (CI, CH4): m/z=325(M+1). Analysis for C19H20N2O3.0.6 H20:Calculated: C, 68.08; H, 6.37; N, 8.36; Found: C, 68.27; H, 6.28; N, 8.01.

Workup

  1. temperatureat reflux under nitrogen for 48 hours
  2. temperatureThe mixture was cooled in an ice bath
  3. filtrationorange crystals were collected by filtration
  4. customThe material was chromatographed with dichloromethane, ethyl ether:dichloromethane (2:98) and ethyl ether:dichloromethane (10:90) as the elutents
  5. customThe solvent was evaporated
  6. customthe residue recrystallized from toluene/hexane

Sources & evidence

ORD record
ord-796f732351984fd7bf193cfd3dc34d2b
Source dataset
uspto-grants-1997_04
Patent number
US05622964

Reaction notes

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