1-(1-oxido-8-phenylmethoxyquinolin-1-ium-5-yl)ethanone

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

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

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

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Acetyl-8-benzyloxyquinoline-N-oxide (10 gms/0.034 moles) was charged in acetic anhydride (20 ml) at 25-30° C. The resulting slurry was heated to 40° C. and stirred for 2 hours at 40° C. After completion of reaction, the reaction mass was cooled to 25-30° C., chilled to 0-5° C. and stirred for 30 minutes at 0-5° C. The resulting 5-Acetyl-8-benzyloxycarbostyril was isolated by filtration and washed with diisopropyl ether (50 ml), dried under vacuum at 60-65° C. for 2-3 hours. Yield-7 gms. After completion of reaction the reaction mass was cooled to 25-30° C. chilled to 0-5° C. stirred for 30 minutes at 0-5° C

Conditions: temp:27.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Acetyl-8-benzyloxyquinoline (200 gms/0.72 moles) was dissolved in dichloromethane (4 liters) at room temperature. To this solution was added m-chloroperoxybenzoic acid (355.64 gms/1.44 moles) in 90 minutes under stiffing. The mixture was stirred at 25-30° C. for 2 hours. After completion of reaction, reaction mass was quenched with 8% sodium bicarbonate solution (3.04 liter) slowly in 30 minutes and stirred for 5-10 minutes at same temperature. The organic layer was separated and aqueous layer was extracted with dichloromethane (2.5 liters). The organic layers were combined and washed with brine solution (2.5 liters). The dichloromethane was distilled out under vacuum at 40° C. The residue was stripped with acetone (500 ml) to remove traces of dichloromethane. The residue was stirred with acetone (200 ml) and chilled to 0-5° C. for 2 hours. The resulting 5-Acetyl-8-benzyloxyquinoline-N-oxide was isolated by filtration and washed with diethyl ether (200 ml), dried under vacuum at 60-65° C. for 2-3 hours. Yield-116 gms. After completion of reaction, reaction mass was quenched with 8% sodium bicarbonate solution (3.04 liter) slowly in 30 minutes stirred for 5-10 minutes at same temperature The organic layer was separated aqueous layer was extracted with dichloromethane (2.5 liters) washed with brine solution (2.5 liters) The dichloromethane was distilled out under vacuum at 40° C to remove traces of dichloromethane The residue was stirred with acetone (200 ml) chilled to 0-5° C. for 2 hours

Conditions: temp:27.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Acetyl-8-benzyloxyquinoline (200 gms/0.72 moles) was dissolved in dichloromethane (4 liters) at room temperature. To this solution was added m-chloroperoxybenzoic acid (355.64 gms/1.44 moles) in 90 minutes under stiffing. The mixture was stirred at 25-30° C. for 2 hours. After completion of reaction, reaction mass was quenched with 8% sodium bicarbonate solution (3.04 liter) slowly in 30 minutes and stirred for 5-10 minutes at same temperature. The organic layer was separated and aqueous layer was extracted with dichloromethane (2.5 liters). The organic layers were combined and washed with brine solution (2.5 liters). The dichloromethane was distilled out under vacuum at 40° C. The residue was stripped with acetone (500 ml) to remove traces of dichloromethane. The residue was stirred with acetone (200 ml) and chilled to 0-5° C. for 2 hours. The resulting 5-Acetyl-8-benzyloxyquinoline-N-oxide was isolated by filtration and washed with diethyl ether (200 ml), dried under vacuum at 60-65° C. for 2-3 hours. Yield-116 gms. After completion of reaction, reaction mass was quenched with 8% sodium bicarbonate solution (3.04 liter) slowly in 30 minutes stirred for 5-10 minutes at same temperature The organic layer was separated aqueous layer was extracted with dichloromethane (2.5 liters) washed with brine solution (2.5 liters) The dichloromethane was distilled out under vacuum at 40° C to remove traces of dichloromethane The residue was stirred with acetone (200 ml) chilled to 0-5° C. for 2 hours

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

Procedure: 5 g of 5-acetyl-8-benzyloxyquinoline are dissolved in 50 ml of chloroform. The solution is ice-cooled and 3.12 g of 80% m-chloroperbenzoic acid are added thereto under stirring. The mixture is stirred at room temperature for 24 hours and at 50° C. for 7.5 hours. The mixture is then stirred at room temperature for 64 hours. 2 g of 80% m-chloroperbenzoic acid are further added to the mixture during the reaction. After the reaction, chloroform is added to the mixture. The mixture is washed with water, a 4% sodium bicarbonate solution and a saturated sodium chloride solution, dried and then evaporated under reduced pressure to remove chloroform. 5-Acetyl-8-benzyloxyquinoline-N-oxide is obtained as yellow solid. cooled The mixture is stirred at room temperature for 24 hours and at 50° C. for 7.5 hours The mixture is then stirred at room temperature for 64 hours is added to the mixture The mixture is washed with water a 4% sodium bicarbonate solution and a saturated sodium chloride solution, dried evaporated under reduced pressure to remove chloroform

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

Procedure: 5 g of 5-acetyl-8-benzyloxyquinoline are dissolved in 50 ml of chloroform. The solution is ice-cooled and 3.12 g of 80% m-chloroperbenzoic acid are added thereto under stirring. The mixture is stirred at room temperature for 24 hours and at 50° C. for 7.5 hours. The mixture is then stirred at room temperature for 64 hours. 2 g of 80% m-chloroperbenzoic acid are further added to the mixture during the reaction. After the reaction, chloroform is added to the mixture. The mixture is washed with water, a 4% sodium bicarbonate solution and a saturated sodium chloride solution, dried and then evaporated under reduced pressure to remove chloroform. 5-Acetyl-8-benzyloxyquinoline-N-oxide is obtained as yellow solid. cooled The mixture is stirred at room temperature for 24 hours and at 50° C. for 7.5 hours The mixture is then stirred at room temperature for 64 hours is added to the mixture The mixture is washed with water a 4% sodium bicarbonate solution and a saturated sodium chloride solution, dried evaporated under reduced pressure to remove chloroform

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Acetyl-8-benzyloxyquinoline-N-oxide (10 gms/0.034 moles) was charged in acetic anhydride (20 ml) at 25-30° C. The resulting slurry was heated to 40° C. and stirred for 2 hours at 40° C. After completion of reaction, the reaction mass was cooled to 25-30° C., chilled to 0-5° C. and stirred for 30 minutes at 0-5° C. The resulting 5-Acetyl-8-benzyloxycarbostyril was isolated by filtration and washed with diisopropyl ether (50 ml), dried under vacuum at 60-65° C. for 2-3 hours. Yield-7 gms. After completion of reaction the reaction mass was cooled to 25-30° C. chilled to 0-5° C. stirred for 30 minutes at 0-5° C

Conditions: temp:27.51; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 5-Acetyl-8-benzyloxyquinoline (200 gms/0.72 moles) was dissolved in dichloromethane (4 liters) at room temperature. To this solution was added m-chloroperoxybenzoic acid (355.64 gms/1.44 moles) in 90 minutes under stiffing. The mixture was stirred at 25-30° C. for 2 hours. After completion of reaction, reaction mass was quenched with 8% sodium bicarbonate solution (3.04 liter) slowly in 30 minutes and stirred for 5-10 minutes at same temperature. The organic layer was separated and aqueous layer was extracted with dichloromethane (2.5 liters). The organic layers were combined and washed with brine solution (2.5 liters). The dichloromethane was distilled out under vacuum at 40° C. The residue was stripped with acetone (500 ml) to remove traces of dichloromethane. The residue was stirred with acetone (200 ml) and chilled to 0-5° C. for 2 hours. The resulting 5-Acetyl-8-benzyloxyquinoline-N-oxide was isolated by filtration and washed with diethyl ether (200 ml), dried under vacuum at 60-65° C. for 2-3 hours. Yield-116 gms. After completion of reaction, reaction mass was quenched with 8% sodium bicarbonate solution (3.04 liter) slowly in 30 minutes stirred for 5-10 minutes at same temperature The organic layer was separated aqueous layer was extracted with dichloromethane (2.5 liters) washed with brine solution (2.5 liters) The dichloromethane was distilled out under vacuum at 40° C to remove traces of dichloromethane The residue was stirred with acetone (200 ml) chilled to 0-5° C. for 2 hours