Nitric Acid → 5,6-Dimethyl-3-nitro-1,2-dihydropyridin-2-one

HRID 489259Notes

Reaction equation

HRID 489259 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5](=[O:9])[NH:6][C:7]=1[CH3:8].[N+:10]([O-])([OH:12])=[O:11]>S(=O)(=O)(O)O>[CH3:1][C:2]1[CH:3]=[C:4]([N+:10]([O-:12])=[O:11])[C:5](=[O:9])[NH:6][C:7]=1[CH3:8]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 1197855,6-Dimethyl-2-pyridone

Product 1

HCID 2646205,6-Dimethyl-3-nitro-1,2-dihydropyridin-2-oneYield 61.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

5,6-Dimethyl-2-pyridone (1-013-03) (3.695 g) was dissolved in conc. sulfuric acid (38 mL) under ice-cooling, and the reaction mixture was stirred under ice-cooling, and then to the reaction mixture was added dropwise 70% nitric acid (3.53 mL) at 3 to 5° C. as internal temperature for 50 min, and then the reaction mixture was stirred. After 2 h, the reaction mixture was poured gradually into ice and the resulting crystal was filtered. The crystal was washed with water to give 5,6-dimethyl-3-nitro-2-pyridone (1-013-04) (3.102 g, 61.5%, m.p.:251-257 (dec)). Furthermore the aqueous layer was extracted five times with chloroform, the organic layer was dried over magnesium sulfate, and evaporated under reduced pressure. The resulting crystal was filtered to give an additional 5,6-dimethyl-3-nitro-2-pyridone (1-013-04)(271 mg, 5.4%).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe reaction mixture was stirred
  4. additionthe reaction mixture was poured gradually into ice
  5. filtrationthe resulting crystal was filtered
  6. washThe crystal was washed with water

Sources & evidence

ORD record
ord-caec8589d10443f9a234f82df292f136
Source dataset
uspto-grants-2005_12
Patent number
US06977266B2

Reaction notes

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