4-methyl-3,4-dihydro-1H-quinolin-2-one

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

Procedure: A solution of bromine (0.08 cm3) in acetic acid (1 cm3) was added at room temperature to a stirred solution of 4-methyl-3,4-dihydro-2-(1H)-quinolone (0.5 g) in acetic acid (4.0 cm3). After 2 hours, volatile material was removed in vacuo, the residue was partitioned between chloroform (50 cm3) and water (20 cm3), and the organic phase was further extracted with chloroform (2×20 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo and the solid residue was recrystallised from ethyl acetate to afford 6-bromo-4-methyl-3,4-dihydro-2-(1H)-quinolone, m.p. 190°, (0.35 g). volatile material was removed in vacuo the residue was partitioned between chloroform (50 cm3) and water (20 cm3) the organic phase was further extracted with chloroform (2×20 cm3) dried (MgSO4) organic extracts were evaporated in vacuo the solid residue was recrystallised from ethyl acetate

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

Procedure: A solution of bromine (0.08 cm3) in acetic acid (1 cm3) was added at room temperature to a stirred solution of 4-methyl-3,4-dihydro-2-(1H)-quinolone (0.5 g) in acetic acid (4.0 cm3). After 2 hours, volatile material was removed in vacuo, the residue was partitioned between chloroform (50 cm3) and water (20 cm3), and the organic phase was further extracted with chloroform (2×20 cm3). The combined and dried (MgSO4) organic extracts were evaporated in vacuo and the solid residue was recrystallised from ethyl acetate to afford 6-bromo-4-methyl-3,4-dihydro-2-(1H)-quinolone, m.p. 190°, (0.35 g). volatile material was removed in vacuo the residue was partitioned between chloroform (50 cm3) and water (20 cm3) the organic phase was further extracted with chloroform (2×20 cm3) dried (MgSO4) organic extracts were evaporated in vacuo the solid residue was recrystallised from ethyl acetate