1-[3-(2-Methoxy-5-nitro-phenyl)-pyrrolidin-1-yl]-propan-1-one → 1-[3-(2-Methoxy-5-amino-phenyl)-pyrrolidin-1-yl]-propan-1-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[CH:12]1[CH2:16][CH2:15][N:14]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:13]1>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[CH:12]1[CH2:16][CH2:15][N:14]([C:17](=[O:20])[CH2:18][CH3:19])[CH2:13]1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
1-[3-(2-Methoxy-5-nitro-phenyl)-pyrrolidin-1-yl]-propan-1-one (0.85 g; 3.05 mmol) were dissolved in 50 ml methanol. 3.65 g of stannous dichloride (16.18 mmol) were added and the reaction mixture was stirred for 2 h under refluxing conditions. When the starting material was consumed, the solvent was evaporated under reduced pressure and the residue was treated with a mixture of 1 N aqueous NaOH/ethyl acetate and filtered. Phases were separated, the aqueous phase was extracted with ethyl acetate and the combined organic layers were dried over magnesium sulfate, filtered and evaporated to dryness to yield 0.44 g of crude product which was used in the next reaction without further purification.
Workup
- customWhen the starting material was consumed
- customthe solvent was evaporated under reduced pressure
- additionthe residue was treated with a mixture of 1 N aqueous NaOH/ethyl acetate
- filtrationfiltered
- customPhases were separated
- extractionthe aqueous phase was extracted with ethyl acetate
- dry with materialthe combined organic layers were dried over magnesium sulfate
- filtrationfiltered
- customevaporated to dryness
Sources & evidence
- ORD record
- ord-0d7e0e2490b240e3b8c3f6b6e89aa28f
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08642642B2
Reaction notes
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