Nitric Acid → HCID 10353055, compound

HRID 1033026Notes

Reaction equation

HRID 1033026 reaction equation
[CH2:1]([C:5]1[CH:6]=[CH:7][C:8](=[O:12])[NH:9][C:10]=1[CH3:11])[CH2:2][CH2:3][CH3:4].[N+:13]([O-])([OH:15])=[O:14]>S(=O)(=O)(O)O>[N+:13]([C:7]1[C:8](=[O:12])[NH:9][C:10]([CH3:11])=[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=1)([O-:15])=[O:14]

Participants

4

Reactant 2

HCID 944Nitric AcidHCID 104646792(1H)-Pyridinone, 5-butyl-6-methyl-

Product 1

HCID 10353055HCID 10353055, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of 5-butyl-6-methylpyridin-2(1H)-one (562 mg, 3.40 mmol) in concentrated sulfuric acid (4.3 mL) was cooled in an ice bath and 70% nitric acid (0.4 mL) was added dropwise. After one hour, the reaction mixture was poured into ice/water and the yellow product extracted into methylene chloride. This solution was dried, filtered and evaporated. The residue (468 mg) was chromatographed on silica gel eluting with 1-2% methanol/chloroform to yield 293 mg (41%) of pure product.

Workup

  1. extractionthe yellow product extracted into methylene chloride
  2. customThis solution was dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue (468 mg) was chromatographed on silica gel eluting with 1-2% methanol/chloroform

Sources & evidence

ORD record
ord-0e063699c9a642ef8a4c65c13bdb4a53
Source dataset
uspto-grants-1994_05
Patent number
US05308854

Reaction notes

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