Nitric Acid → HCID 118061337, compound

HRID 632753Notes

Reaction equation

HRID 632753 reaction equation
[CH3:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[CH:11]=[CH:10][N:9]([CH3:12])[N:8]=2)[C:3]1=[O:13].[N+:14]([O-])([OH:16])=[O:15].C(=O)([O-])O.[Na+]>C(OC(=O)C)(=O)C>[CH3:1][CH:2]1[CH2:6][CH2:5][N:4]([C:7]2[C:11]([N+:14]([O-:16])=[O:15])=[CH:10][N:9]([CH3:12])[N:8]=2)[C:3]1=[O:13]

Participants

5

Reactant 3

HCID 944Nitric AcidHCID 516892Sodium BicarbonateHCID 118061154HCID 118061154, compound

Product 1

HCID 118061337HCID 118061337, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a solution of 3-methyl-1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-one (97 mg) in acetic anhydride (1.2 mL) was added fuming nitric acid (45 μL) under ice-cooling, and the mixture was stirred under ice-cooling for 1.5 hr. The reaction mixture was poured into ice water, and the mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (53 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1.5 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-791d6fcbed544cf49fe88dcfee87a0f7
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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