Ammonia → HCID 23499219, compound

HRID 361398

Reaction equation

HRID 361398 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][CH2:5][C:4](=O)[CH2:3]1.C[N:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=C([N+]([O-])=O)C1=O.N>>[CH3:1][CH:2]1[CH2:3][C:4]2[N:10]=[CH:15][C:14]([N+:16]([O-:18])=[O:17])=[CH:13][C:5]=2[CH2:6][CH2:7]1

Participants

4

Reactant 3

HCID 222AmmoniaHCID 115673-MethylcyclohexanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 23499219HCID 23499219, compoundYield 63%

Procedure

3-Methylcyclohexanone (0.56 g, 4.99 mmol) was mixed with 1-methyl-3,5-dinitro-2-pyridone (1.00 g, 5.02 mmol) in 1M methanolic ammonia (50 mL, 50 mmol) and heated at reflux overnight. The solvent was evaporated off and the residue was suspended in CHCl3 and flash chromatographed over silica gel (43 g) eluting with EtOAc/hexane (1:10) to afford a white solid (515 mg, 63% yield): mp 55°-56° C.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. customThe solvent was evaporated off
  4. customflash chromatographed over silica gel (43 g)
  5. washeluting with EtOAc/hexane (1:10)

Sources & evidence

ORD record
ord-13de913f451144cd924cfe70ddbe691b
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Linked notes

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