8-Chloro-3,4-dihydroquinolin-2(1H)-one

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

Procedure: To a solution of 8-chloro-3,4-dihydro-2(1H)-quinolinone (5.08 g) in acetic anhydride (50 ml) was dropwise added a solution of nitric acid (d=1.40, 2.97 g) in acetic acid (20 ml) over the period of 10 minutes with stirring under ice-cooling. The mixture was stirred for 2 hours at ambient temperature and then for 6 hours at 50° C., and was allowed to stand for 60 hours at ambient temperature. The resulting precipitates were collected, washed with acetic anhydride and ethyl acetate successively and dried to give 8-chloro-6-nitro-3,4-dihydro-2(1H)-quinolinone (3.83 g). cooling The mixture was stirred for 2 hours at ambient temperature to stand for 60 hours at ambient temperature The resulting precipitates were collected washed with acetic anhydride and ethyl acetate successively dried

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

Procedure: To a solution of α-bromopropionyl bromide (60 g) and aluminum chloride (40 g) in carbon disulfide (100 ml) was added 8-chloro-3,4-dihydrocarbostyril (10 g). After refluxing the mixture for 5 hours, carbon disulfide was evaporated and heated at 70° to 80° C. for 5 hours. The reaction mixture was poured into ice water and allowed to stand overnight. The mixture was extracted with chloroform and the chloroform layer was washed with water, dried and treated with activated carbon followed by evaporating chloroform. The residue was washed with diethyl ether and collected by filtration. The residue gave uniform crude crystals upon TLC. The crystals thus obtained were re-crystallized from methanol to give 12 g of 8-chloro-6-α-bromopropionyl-3,4-dihydrocarbostyril. After refluxing the mixture for 5 hours carbon disulfide was evaporated heated at 70° to 80° C. for 5 hours The reaction mixture was poured into ice water The mixture was extracted with chloroform the chloroform layer was washed with water dried treated with activated carbon by evaporating chloroform The residue was washed with diethyl ether collected by filtration The residue gave uniform crude crystals upon TLC The crystals thus obtained were re-crystallized from methanol

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

Procedure: To a solution of 8-chloro-3,4-dihydro-2(1H)-quinolinone (5.08 g) in acetic anhydride (50 ml) was dropwise added a solution of nitric acid (d=1.40, 2.97 g) in acetic acid (20 ml) over the period of 10 minutes with stirring under ice-cooling. The mixture was stirred for 2 hours at ambient temperature and then for 6 hours at 50° C., and was allowed to stand for 60 hours at ambient temperature. The resulting precipitates were collected, washed with acetic anhydride and ethyl acetate successively and dried to give 8-chloro-6-nitro-3,4-dihydro-2(1H)-quinolinone (3.83 g). cooling The mixture was stirred for 2 hours at ambient temperature to stand for 60 hours at ambient temperature The resulting precipitates were collected washed with acetic anhydride and ethyl acetate successively dried