6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium tert-butoxide (0.45 g, 4.0 mmol) was added at 0° C. to a solution of 6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 2.0 mmol) in DMF (5 mL). Then, the reaction mixture was stirred at 0° C. for 30 min and methyl iodide (0.18 g, 1.29 mmol) was added. The resulting mixture was then stirred for 2 h before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, the organic layer was dried over anhy. Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90% yield) as a white solid. MS: 274.0 (M+H)+. was added After extraction of the reaction mixture with EtOAc the organic layer was washed with water and brine in sequence Then, the organic layer was dried over anhy Na2SO4 and the solvent was removed under reduced pressure

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium tert-butoxide (0.45 g, 4.0 mmol) was added at 0° C. to a solution of 6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 2.0 mmol) in DMF (5 mL). Then, the reaction mixture was stirred at 0° C. for 30 min and methyl iodide (0.18 g, 1.29 mmol) was added. The resulting mixture was then stirred for 2 h before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, the organic layer was dried over anhy. Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90% yield) as a white solid. MS: 274.0 (M+H)+. was added After extraction of the reaction mixture with EtOAc the organic layer was washed with water and brine in sequence Then, the organic layer was dried over anhy Na2SO4 and the solvent was removed under reduced pressure

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

Procedure: A flame-dried 50-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide (1.0 g, 3.36 mmol) and aluminium chloride (0.67 g, 5.04 mmol). In a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hr. After cooling to room temperature, the reaction mixture was treated with ice-water slowly, and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhy. Na2SO4. After evaporation of the solvent, the residue was purified by recrystallization in EtOAc (2 mL) and gave title compound (0.44 g, 50% yield) as a solid. MS: 260.0 (M+H)+. A flame-dried 50-mL flask equipped with a magnetic stirring bar In a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hr extracted with EtOAc The organic layer was washed with water and brine in sequence dried over anhy After evaporation of the solvent the residue was purified by recrystallization in EtOAc (2 mL)

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium tert-butoxide (0.45 g, 4.0 mmol) was added to a solution of 6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 2.0 mmol) in DMF (5 mL) at 0° C. Then, the reaction mixture was stirred at 0° C. for 30 min and methyl iodide (0.18 g, 1.29 mmol) was added. The resulting mixture was stirred for 2 hours before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, it was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90%) as a white solid. MS: 274.0 (M+H+)+. was added After extraction of the reaction mixture with EtOAc the organic layer was washed with water and brine in sequence Then, it was dried over anhydrous Na2SO4 the solvent was removed under reduced pressure

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

Procedure: A flame-dried 50-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide (1.0 g, 3.36 mmol) and aluminium chloride (0.67 g, 5.04 mmol). In a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hours. After cooling to room temperature, the reaction mixture was treated slowly with ice-water, then extracted with EtOAc. The organic layer was washed with water and brine in sequence and dried over anhydrous Na2SO4. After evaporation of the solvent, the residue was purified by recrystallization from EtOAc (2 mL) which gave title compound (0.44 g, 50%) as a solid. MS: 260.0 (M+H+)+. A flame-dried 50-mL flask equipped with a magnetic stirring bar In a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hours extracted with EtOAc The organic layer was washed with water and brine in sequence dried over anhydrous Na2SO4 After evaporation of the solvent the residue was purified by recrystallization from EtOAc (2 mL) which

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred solution of 6-bromo-7-chloro-3,4-dihydroquinolin-2(1H)-one (110-2; 2.95 g, 0.0113 mol) in toluene (50 mL) was added Lawesson's reagent (2.2 g, 0.00566 mol). Reaction mass was refluxed at 100° C. for 3 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by silica gel (60-120 mesh) column chromatography using 7% ethyl acetate in hexane to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 12.25 (s, 1H), 7.64 (s, 1H), 7.24 (s, 1H), 2.93-2.89 (t, J=6.8 Hz, 2H), 2.80-2.76 (t, J=8.0 Hz, 2H); MS (M+1): 275.8. Reaction mass The reaction mixture was concentrated under reduced pressure the residue was purified by silica gel (60-120 mesh) column chromatography

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

Procedure: To solution of 7-chloro-3,4-dihydroquinolin-2(1H)-one (110-1; 2.92 g, 0.016 mol) in N,N-dimethylformamide (30 mL), was added N-bromosuccinimide (3.14 g, 0.0176 mol) portion-wise at room temperature. The resulting mixture was stirred at room temperature for 16 h. After 16 h, the reaction mixture was diluted with cold water, solid get precipitated, filtered the solid, washed the solid with water and dried under reduced pressure to afford the compound. 1H NMR (400 MHz, DMSO-d6) δ 10.20 (s, 1H), 7.56 (s, 1H), 7.01 (s, 1H), 2.87-2.84 (t, J=7.2 Hz, 2H), 2.45-2.41 (t, J=7.6 Hz, 2H); MS (M+1): 259.9. After 16 h get precipitated filtered the solid washed the solid with water dried under reduced pressure to afford the compound

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Potassium tert-butoxide (0.45 g, 4.0 mmol) was added at 0° C. to a solution of 6-bromo-7-chloro-3,4-dihydro-1H-quinolin-2-one (0.52 g, 2.0 mmol) in DMF (5 mL). Then, the reaction mixture was stirred at 0° C. for 30 min and methyl iodide (0.18 g, 1.29 mmol) was added. The resulting mixture was then stirred for 2 h before water was added. After extraction of the reaction mixture with EtOAc, the organic layer was washed with water and brine in sequence. Then, the organic layer was dried over anhy. Na2SO4 and the solvent was removed under reduced pressure to give a crude product (0.49 g, 90% yield) as a white solid. MS: 274.0 (M+H)+. was added After extraction of the reaction mixture with EtOAc the organic layer was washed with water and brine in sequence Then, the organic layer was dried over anhy Na2SO4 and the solvent was removed under reduced pressure

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

Procedure: A flame-dried 50-mL flask equipped with a magnetic stirring bar was charged with N-(4-bromo-3-chloro-phenyl)-3-chloro-propionamide (1.0 g, 3.36 mmol) and aluminium chloride (0.67 g, 5.04 mmol). In a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hr. After cooling to room temperature, the reaction mixture was treated with ice-water slowly, and extracted with EtOAc. The organic layer was washed with water and brine in sequence, dried over anhy. Na2SO4. After evaporation of the solvent, the residue was purified by recrystallization in EtOAc (2 mL) and gave title compound (0.44 g, 50% yield) as a solid. MS: 260.0 (M+H)+. A flame-dried 50-mL flask equipped with a magnetic stirring bar In a pre-heated oil bath, the flask was heated at 135˜140° C. for 2 hr extracted with EtOAc The organic layer was washed with water and brine in sequence dried over anhy After evaporation of the solvent the residue was purified by recrystallization in EtOAc (2 mL)