4-methoxy-2,3-dimethyl-1-oxidopyridin-1-ium

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g (0.015 mol) of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of abs. methanol is treated with 0.883 g of sodium methylate, whereupon the mixture is stirred at room temperature under argon for 2 days. The reaction mixture is concentrated and the residue is extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase is dried and evaporated. The residue, crystallized from methylene chloride/ ether, gives 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80°-83°. The reaction mixture is concentrated the residue is extracted with methylene chloride and saturated sodium chloride solution The methylene chloride phase is dried evaporated The residue, crystallized from methylene chloride/ ether

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of absolute methanol was treated with 0.883 g of sodium methylate, whereupon the mixture was stirred at room temperature under argon for 2 days. The reaction mixture was concentrated and the residue was extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase was dried and evaporated. The residue, crystallized from methylene chloride/ether, gave 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80°-83°. The reaction mixture was concentrated the residue was extracted with methylene chloride and saturated sodium chloride solution The methylene chloride phase was dried evaporated The residue, crystallized from methylene chloride/ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of absolute methanol was treated with 0.883 g of sodium methylate, whereupon the mixture was stirred at room temperature under argon for 2 days. The reaction mixture was concentrated and the residue was extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase was dried and evaporated. The residue, crystallized from methylene chloride/ether, gave 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80-83°. The reaction mixture was concentrated the residue was extracted with methylene chloride and saturated sodium chloride solution The methylene chloride phase was dried evaporated The residue, crystallized from methylene chloride/ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g (0.015 mol) of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of abs. methanol is treated with 0.883 g of sodium methylate, whereupon the mixture is stirred at room temperature under argon for 2 days. The reaction mixture is concentrated and the residue is extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase is dried and evaporated. The residue, crystallized from methylene chloride/ ether, gives 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80°-83°. The reaction mixture is concentrated the residue is extracted with methylene chloride and saturated sodium chloride solution The methylene chloride phase is dried evaporated The residue, crystallized from methylene chloride/ ether

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g (0.015 mol) of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of abs. methanol is treated with 0.883 g of sodium methylate, whereupon the mixture is stirred at room temperature under argon for 2 days. The reaction mixture is concentrated and the residue is extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase is dried and evaporated. The residue, crystallized from methylene chloride/ ether, gives 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80°-83°. The reaction mixture is concentrated the residue is extracted with methylene chloride and saturated sodium chloride solution The methylene chloride phase is dried evaporated The residue, crystallized from methylene chloride/ ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 2,3-Dimethyl-4-nitropyridine-1-oxide (5 g) was dissolved in methanol (30 ml). To the solution were added tetrabutylammonium bromide (0.5 g) and potassium hydrogen carbonate (5.6 g), and the mixture was heated (temperature 80°-85° C.) under reflux with stirring for 10 hours. The solid matter was removed from the reaction mixture by filtration, and the filtrate was concentrated and applied to a silica gel (100 g) column. Elution with methanol-dichloromethane (1:9) and recrystallization from ethyl acetate-hexane gave 4.3 g of white 2,3-dimethyl-4-methoxypyridine-1-oxide. Melting point 85°-86° C. the mixture was heated (temperature 80°-85° C.) under reflux The solid matter was removed from the reaction mixture by filtration the filtrate was concentrated Elution with methanol-dichloromethane (1:9) and recrystallization from ethyl acetate-hexane

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To 37.2 g of 4-methoxy-2,3-dimethylpyridine-1-oxide, 55.0 g (5.0 eq.) of acetic anhydride was added, and the mixture was allowed to react for 3 hours at 90 to 100° C. Acetic anhydride was distilled off, and then the resulting concentrated residue was purified on a silica gel column, to obtain 15.8 g of 2-acetoxymethyl-3-methyl-4-methoxy-pyridine as an oily matter. to react for 3 hours at 90 to 100° C Acetic anhydride was distilled off the resulting concentrated residue was purified on a silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution prepared by diluting 41.6 g (2.0 eq.) of a 28% aqueous solution of sodium methoxide with 200 mL of dimethylsulfoxide, a liquid containing 17.0 g of 4-chlor-2,3-dimethylpyridine-1-oxide dissolved in dimethylsulfoxide (70 mL) was added dropwise. The mixture was allowed to react for 3 hours at 40 to 50° C., and then was left to stand overnight at room temperature. 15 mL of water was added to the reaction liquid, and the mixture was concentrated, to obtain a residue in the form of a black paste. Subsequently, the residue was dissolved in 500 mL of water, and then the aqueous solution was extracted three times with 670 mL of chloroform. The extract was dried over anhydrous magnesium sulfate, and then was concentrated to dryness under reduced pressure, to obtain 37.2 g of 4-methoxy-2,3-dimethylpyridine-1-oxide. To a solution prepared was added dropwise to react for 3 hours at 40 to 50° C. was left the mixture was concentrated to obtain a residue in the form of a black paste the aqueous solution was extracted three times with 670 mL of chloroform The extract was dried over anhydrous magnesium sulfate was concentrated to dryness under reduced pressure

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of absolute methanol was treated with 0.883 g of sodium methylate, whereupon the mixture was stirred at room temperature under argon for 2 days. The reaction mixture was concentrated and the residue was extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase was dried and evaporated. The residue, crystallized from methylene chloride/ether, gave 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80°-83°. The reaction mixture was concentrated the residue was extracted with methylene chloride and saturated sodium chloride solution The methylene chloride phase was dried evaporated The residue, crystallized from methylene chloride/ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of 2.5 g of 2,3-dimethyl-4-nitropyridine 1-oxide in 50 ml of absolute methanol was treated with 0.883 g of sodium methylate, whereupon the mixture was stirred at room temperature under argon for 2 days. The reaction mixture was concentrated and the residue was extracted with methylene chloride and saturated sodium chloride solution. The methylene chloride phase was dried and evaporated. The residue, crystallized from methylene chloride/ether, gave 4-methoxy-2,3-dimethylpyridine 1-oxide of melting point 80-83°. The reaction mixture was concentrated the residue was extracted with methylene chloride and saturated sodium chloride solution The methylene chloride phase was dried evaporated The residue, crystallized from methylene chloride/ether