Nitric Acid → HCID 118061059, compound

HRID 632757Notes

Reaction equation

HRID 632757 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:14][N:13]([C:15]2[CH:19]=[CH:18][N:17]([CH3:20])[N:16]=2)[C:12](=[O:21])[C:11]1([CH3:23])[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OC(=O)C)(=O)C.[N+:31]([O-])([OH:33])=[O:32].[OH-].[Na+]>O>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:14][N:13]([C:15]2[C:19]([N+:31]([O-:33])=[O:32])=[CH:18][N:17]([CH3:20])[N:16]=2)[C:12](=[O:21])[C:11]1([CH3:23])[CH3:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 118061016HCID 118061016, compound

Product 1

HCID 118061059HCID 118061059, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-((benzyloxy)methyl)-3,3-dimethyl-1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-one (459 mg) and acetic anhydride (3.0 mL) was added fuming nitric acid (0.12 mL) under ice-cooling. The reaction mixture was stirred under ice-cooling for 1 hr, water was added thereto, and the mixture was neutralized with 8M aqueous sodium hydroxide solution, and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium 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 (343 mg).

Workup

  1. temperaturecooling
  2. temperaturecooling for 1 hr
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. dry with materialdried over anhydrous sodium 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-6d8981fec2dc48cbac0d4efb9fabed0f
Source dataset
uspto-grants-2016_04
Patent number
US09321757B2

Reaction notes

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