Nitric Acid → 1-[3-(2-Methoxy-5-nitro-phenyl)-pyrrolidin-1-yl]-propan-1-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:10]1.[N+:18]([O-])([OH:20])=[O:19].S(=O)(=O)(O)O.[OH-].[Na+]>[N+](C)([O-])=O.O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:18]([O-:20])=[O:19])=[CH:5][C:4]=1[CH:9]1[CH2:13][CH2:12][N:11]([C:14](=[O:17])[CH2:15][CH3:16])[CH2:10]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
1-[3-(2-Methoxy-phenyl)-pyrrolidin-1-yl]-propan-1-one (0.7 g; 3 mmol) were dissolved in 10 ml of nitromethane. At −5° C. to −10° C., a mixture of 0.290 g nitric acid, 0.5 g water and 5.52 g sulphuric acid were added within 25 minutes, and the reaction mixture was stirred for another 1 h at low temperature and 16 h at room temperature. Ice was added, the reaction mixture was adjusted to alkaline pH with 50% aqueous NaOH, and the aqueous phase was extracted twice with diethylether. The organic layers were combined, dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure to yield 0.85 g of the desired product as a mixture of isomers and small amounts of the dinitro derivative which was used in the next reaction without further purification.
Workup
- additionwere added within 25 minutes
- additionIce was added
- extractionthe aqueous phase was extracted twice with diethylether
- dry with materialdried over magnesium sulfate
- filtrationfiltered
- customthe solvent was evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-973bdd699fa14b72a522e13939755665
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642642B2
Reaction notes
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