Water → HCID 19774538, compound
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][N:7]=[CH:6][C:5]=1[NH+:10]([O-:16])[N:11]1[CH:15]=[CH:14][CH:13]=[CH:12]1)([O-:3])=[O:2].[H-].[Na+].S(OC)(O[CH3:23])(=O)=O.O>CN(C)C=O>[CH3:23][N+:10]([O-:16])([N:11]1[CH:12]=[CH:13][CH:14]=[CH:15]1)[C:5]1[CH:6]=[N:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]Participants
Procedure
A solution of 4-nitro-N-(1H-pyrrol-1-yl)-3-pyridinamine- N-oxide (3.9 g) in 50 ml of dimethylformamide was added to a cooled suspension of sodium hydride (60% oil dispersion, 0.8 g, washed with hexanes) in 5 ml of dimethylformamide. After the anion formation, a solution of dimethyl sulfate (2.7 g) in 5 ml of dimethylformamide was added. After stirring twenty hours at ambient temperature, the reaction mixture was stirred with water and extracted with dichloromethane. The organic extract was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and evaporated to 4.5 g of oil. This oil was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane) to give 4 g of solid, mp 135°-140°. This material was purified by HPLC (silica, 20% ethyl acetate in dichloromethane) to give 3.5 g of solid, mp 140°-144°. This material was recrystallized from absolute ethanol to give 2.1 g of needles, mp 150°-151°.
Workup
- extractionextracted with dichloromethane
- extractionThe organic extract
- washwas washed with water and saturated sodium chloride solution
- dry with materialdried over anhydrous magnesium sulfate
- filtrationfiltered
- customevaporated to 4.5 g of oil
- customThis oil was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane)
Sources & evidence
- ORD record
- ord-5f3d95daf5f544ba86c188f84df615db
- Source dataset
- uspto-grants-1993_03
- Patent number
- US05194618
Reaction notes
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