6-methyl-1-oxidopyridin-1-ium-3-ol

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

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

Procedure: 5-Hydroxy-2-methylpyridine (25 g) was suspended in chloroform (500 ml) and treated with m-chloroperbenzoic acid (57 g of material described as 57-86% pure). After stirring for 1 hour the solution was dried with MgSO4 and poured onto a silica column. Elution with EtOAc to remove byproducts and then with 20-50% EtOH in EtOAc gave the product (27.7 g). was dried with MgSO4 poured onto a silica column Elution with EtOAc to remove byproducts

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

Procedure: 5-Hydroxy-2-methylpyridine (25 g) was suspended in chloroform (500 ml) and treated with m-chloroperbenzoic acid (57 g of material described as 57-86% pure). After stirring for 1 hour the solution was dried with MgSO4 and poured onto a silica column. Elution with EtOAc to remove byproducts and then with 20-50% EtOH in EtOAc gave the product (27.7 g). was dried with MgSO4 poured onto a silica column Elution with EtOAc to remove byproducts

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

Procedure: A mixture of 100.0 g of 2-methyl-5-hydroxy-pyridine, 600 ml of acetic acid and 200 ml of 30-35% hydrogen peroxide is heated on a steam bath with occasional swirling for 18 hours. Then to the mixture is added 500 ml of water and the resulting solution is evaporated to leave a residue. The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid. This solid is recrystallized from ethanol to give 2-methyl-5-hydroxy-pyridine-1-oxide melting at 185°-187°. is heated on a steam bath the resulting solution is evaporated to leave a residue The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid This solid is recrystallized from ethanol

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

Procedure: A mixture of 100.0 g of 2-methyl-5-hydroxy-pyridine, 600 ml of acetic acid and 200 ml of 30-35% hydrogen peroxide is heated on a steam bath with occasional swirling for 18 hours. Then to the mixture is added 500 ml of water and the resulting solution is evaporated to leave a residue. The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid. This solid is recrystallized from ethanol to give 2-methyl-5-hydroxy-pyridine-1-oxide melting at 185°-187°. is heated on a steam bath the resulting solution is evaporated to leave a residue The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid This solid is recrystallized from ethanol

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

Procedure: A mixture of 100.0 g of 2-methyl-5-hydroxy-pyridine, 600 ml of acetic acid and 200 ml of 30-35% hydrogen peroxide is heated on a steam bath with occasional swirling for 18 hours. Then to the mixture is added 500 ml of water and the resulting solution is evaporated to leave a residue. The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid. This solid is recrystallized from ethanol to give 2-methyl-5-hydroxy-pyridine-1-oxide melting at 185°-187°. is heated on a steam bath the resulting solution is evaporated to leave a residue The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid This solid is recrystallized from ethanol

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

Procedure: A solution of the pyridine N-oxide (a) (21.12 g) in DMF (450 ml) was treated with potassium carbonate (26.2 g) then, after 30 minutes, with methyl bromoacetate (16 ml), and stirred overnight. Solvent was evaporated, saturated brine (500 ml) added and the mixture extracted with chloroform (6×200 ml). The combined organic solution was dried and evaporated and the residue chromatographed (20% EtOH in EtOAc) to give a solid (18.5 g). Solvent was evaporated saturated brine (500 ml) added the mixture extracted with chloroform (6×200 ml) The combined organic solution was dried evaporated the residue chromatographed (20% EtOH in EtOAc)

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

Procedure: 5-Hydroxy-2-methylpyridine (25 g) was suspended in chloroform (500 ml) and treated with m-chloroperbenzoic acid (57 g of material described by the manufacturer as 57-86% pure). After stirring for 1 hour the solution was dried with MgSO4 and poured onto a silica column. Elution with EtOAc to remove byproducts and then with 20-50% EtOH in EtOAc gave a solid (27.7 g). was dried with MgSO4 poured onto a silica column Elution with EtOAc to remove byproducts

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

Procedure: A mixture of 100.0 g of 2-methyl-5-hydroxy-pyridine, 600 ml of acetic acid and 200 ml of 30-35% hydrogen peroxide is heated on a steam bath with occasional swirling for 18 hours. Then to the mixture is added 500 ml of water and the resulting solution is evaporated to leave a residue. The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid. This solid is recrystallized from ethanol to give 2-methyl-5-hydroxy-pyridine-1-oxide melting at 185°-187°. is heated on a steam bath the resulting solution is evaporated to leave a residue The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid This solid is recrystallized from ethanol

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

Procedure: 5-Hydroxy-2-methylpyridine (25 g) was suspended in chloroform (500 ml) and treated with m-chloroperbenzoic acid (57 g of material described as 57-86% pure). After stirring for 1 hour the solution was dried with MgSO4 and poured onto a silica column. Elution with EtOAc to remove byproducts and then with 20-50% EtOH in EtOAc gave the product (27.7 g). was dried with MgSO4 poured onto a silica column Elution with EtOAc to remove byproducts

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

Procedure: A mixture of 100.0 g of 2-methyl-5-hydroxy-pyridine, 600 ml of acetic acid and 200 ml of 30-35% hydrogen peroxide is heated on a steam bath with occasional swirling for 18 hours. Then to the mixture is added 500 ml of water and the resulting solution is evaporated to leave a residue. The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid. This solid is recrystallized from ethanol to give 2-methyl-5-hydroxy-pyridine-1-oxide melting at 185°-187°. is heated on a steam bath the resulting solution is evaporated to leave a residue The last traces of water from the residue are removed azeotropically with isopropanol to give a yellow solid This solid is recrystallized from ethanol