Ammonia → HCID 10966069, compound

HRID 2187529Notes

Reaction equation

HRID 2187529 reaction equation
[N+]([C:4]1[C:5](=O)[N:6](C)[CH:7]=[C:8]([N+:10]([O-:12])=[O:11])[CH:9]=1)([O-])=O.N.[CH3:16][N:17]1[CH2:22]C[C:20](=O)[C:19](C)([CH3:24])[CH2:18]1>CO>[N+:10]([C:8]1[CH:7]=[N:6][C:5]2[C:19]([CH3:24])([CH3:20])[CH2:18][N:17]([CH3:22])[CH2:16][C:4]=2[CH:9]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 36212361-Methyl-3,5-dinitro-1H-pyridin-2-oneHCID 13556123HCID 13556123, compound

Product 1

HCID 10966069HCID 10966069, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

3,5-Dinitro-1-methylpyridin-2-one [prepared by the method of E. Matsumura, M. Ariga and Y. Tohda. Bull. Chem. Soc. Japan, 1979, 52, 2413-2419] (2 g; 10 mmol) was suspended in MeOH (50 ml) and treated with 0.88 aq, ammonia (10 ml; 157 mmol). 1,3,3-Trimethylpiperidin-4-one (1.7 g; 12 mmol) was added and the mixture heated at 70° C. for 5 h. The mixture was cooled to room temperature then evaporated to dryness in vacuo. The residue was digested with dichloromethane (2×50 ml) and the hot solution decanted from the red gum. The extracts were combined, evaporated to dryness in vacuo and the residue purified by chromatography on SiO2, with 50% ethyl acetate: 60-80° C. petroleum to give the title compound as a yellow oil, which solidified on standing (1.05 g; 48%).

Workup

  1. additiontreated with 0.88 aq
  2. temperatureThe mixture was cooled to room temperature
  3. customthen evaporated to dryness in vacuo
  4. customthe hot solution decanted from the red gum
  5. customevaporated to dryness in vacuo
  6. customthe residue purified by chromatography on SiO2, with 50% ethyl acetate

Sources & evidence

ORD record
ord-d9986a1d9f4b40c7af69f1ad8634547a
Source dataset
uspto-grants-2002_06
Patent number
US06410555B1

Reaction notes

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