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Nitric Acid → 4-((benzyloxy)methyl)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one

HRID 632755
Notes
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Reaction equation

HRID 632755 reaction equation
[N+:1]([O-:4])(O)=[O:2].C(OC(=O)C)(=O)C.[CH2:12]([O:19][CH2:20][CH:21]1[CH2:25][N:24]([C:26]2[CH:30]=[CH:29][N:28]([CH3:31])[N:27]=2)[C:23](=[O:32])[CH2:22]1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[OH-].[Na+]>O>[CH2:12]([O:19][CH2:20][CH:21]1[CH2:25][N:24]([C:26]2[C:30]([N+:1]([O-:4])=[O:2])=[CH:29][N:28]([CH3:31])[N:27]=2)[C:23](=[O:32])[CH2:22]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 944Nitric AcidHCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 1180612464-((benzyloxy)methyl)-1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-one

Product 1

HCID 1180607804-((benzyloxy)methyl)-1-(1-methyl-4-nitro-1H-pyrazol-3-yl)pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

To a mixture of fuming nitric acid (0.32 mL) and acetic anhydride (5.0 mL) was added 4-((benzyloxy)methyl)-1-(1-methyl-1H-pyrazol-3-yl)pyrrolidin-2-one (1.1 g) 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 (1.1 g).

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-3259c3e34ab44f0483cd556466cca767
Source dataset
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09321757B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes