Ammonia → HCID 15462861, compound

HRID 361397Notes

Reaction equation

HRID 361397 reaction equation
[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=O)[CH2:4][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>C(Cl)(Cl)Cl>[CH3:1][CH:2]1[CH2:7][CH2:6][C:5]2[N:10]=[CH:15][C:14]([N+:16]([O-:18])=[O:17])=[CH:13][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 115254-MethylcyclohexanoneHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-one

Product 1

HCID 15462861HCID 15462861, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Methylcyclohexanone (170 mg, 1.52 mmol) was mixed with 1-methyl-3,5-dinitro-2-pyridone (300 mg, 1.51 mmol) in 1M methanolic ammonia (30 mL, 30 mmol). The solution was heated at gentle reflux for 3 h. Evaporation of the solvent gave an orange residue which was suspended in CHCl3 and flash chromatographed over silica gel (16 g) eluting with EtOAc/hexane (1:10) to afford a white solid (211 mg, 73% yield): mp 50°-52° C.

Workup

  1. temperatureThe solution was heated
  2. temperatureat gentle reflux for 3 h
  3. customEvaporation of the solvent
  4. customgave an orange residue which
  5. customflash chromatographed over silica gel (16 g)
  6. washeluting with EtOAc/hexane (1:10)

Sources & evidence

ORD record
ord-248af8e751054f88bb128f9377438adf
Source dataset
uspto-grants-1999_02
Patent number
US05866579

Reaction notes

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