Water → HCID 19774538, compound

HRID 1086893Notes

Reaction equation

HRID 1086893 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

6

Reactant 4

HCID 962WaterHCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 197745754-nitro-N-(1H-pyrrol-1-yl)-3-pyridinamine-N-oxide

Product 1

HCID 19774538HCID 19774538, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

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

  1. extractionextracted with dichloromethane
  2. extractionThe organic extract
  3. washwas washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated to 4.5 g of oil
  7. customThis oil was purified by flash chromatography (silica, 10% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-5a8740edb66d462f9174e0e9033f6b77
Source dataset
uspto-grants-1991_07
Patent number
US05032599

Reaction notes

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