6-bromo-2,3-dihydro-1H-quinolin-4-one

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

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

Procedure: 45.2 Parts of 6-bromo-4-oxo-1,2,3,4-tetrahydroquinoline and 200 parts of dioxane were mixed, and 39.4 parts of phosgene was introduced to the stirred mixture while the temperature was maintained at 20°-25° C. over about 30 minutes. After the introduction, the reaction was effected at 40°-45° C. for 2.5 hours, and thereafter the mixture was treated as in Example 37 (a) to obtain 55.9 parts of 6-bromo-4-oxo-1-chloroformyl-1,2,3,4-tetrahydroquinoline. was maintained at 20°-25° C. over about 30 minutes

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

Procedure: 45.2 Parts of 6-bromo-4-oxo-1,2,3,4-tetrahydroquinoline and 200 parts of dioxane were mixed, and 39.4 parts of phosgene was introduced to the stirred mixture while the temperature was maintained at 20°-25° C. over about 30 minutes. After the introduction, the reaction was effected at 40°-45° C. for 2.5 hours, and thereafter the mixture was treated as in Example 37 (a) to obtain 55.9 parts of 6-bromo-4-oxo-1-chloroformyl-1,2,3,4-tetrahydroquinoline. was maintained at 20°-25° C. over about 30 minutes

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

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

Procedure: To a solution of 2,3-dihydroquinolin-4(1H)-one (2.94 g) in dichloromethane (25 mL) was added N-bromosuccinimide (3.63 g). The mixture was stirred at room temperature for 1.5 h and was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution and gave 4.14 g of the title compound. MS (ESI−) for C9H8BrNO m/z 225.77 (M−H)−. was partitioned between aqueous sodium bicarbonate and dichloromethane The organic layer was washed with brine dried with sodium sulfate filtered concentrated The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution

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

Procedure: To a solution of 2,3-dihydroquinolin-4(1H)-one (2.94 g) in dichloromethane (25 mL) was added N-bromosuccinimide (3.63 g). The mixture was stirred at room temperature for 1.5 h and was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution and gave 4.14 g of the title compound. MS (ESI−) for C9H8BrNO m/z 225.77 (M−H)−. was partitioned between aqueous sodium bicarbonate and dichloromethane The organic layer was washed with brine dried with sodium sulfate filtered concentrated The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution

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

Procedure: To a solution of 2,3-dihydroquinolin-4(1H)-one (2.94 g) in dichloromethane (25 mL) was added N-bromosuccinimide (3.63 g). The mixture was stirred at room temperature for 1.5 h and was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was washed with brine, dried with sodium sulfate, filtered, and concentrated. The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution and gave 4.14 g of the title compound. MS (ESI−) for C9H8BrNO m/z 225.77 (M−H)−. was partitioned between aqueous sodium bicarbonate and dichloromethane The organic layer was washed with brine dried with sodium sulfate filtered concentrated The concentrate was chromatographed on silica gel using a 35% ethyl acetate in heptane solvent solution

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

Procedure: 45.2 Parts of 6-bromo-4-oxo-1,2,3,4-tetrahydroquinoline and 200 parts of dioxane were mixed, and 39.4 parts of phosgene was introduced to the stirred mixture while the temperature was maintained at 20°-25° C. over about 30 minutes. After the introduction, the reaction was effected at 40°-45° C. for 2.5 hours, and thereafter the mixture was treated as in Example 37 (a) to obtain 55.9 parts of 6-bromo-4-oxo-1-chloroformyl-1,2,3,4-tetrahydroquinoline. was maintained at 20°-25° C. over about 30 minutes