2-bromo-1-(2-methylphenyl)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:0.00; pressure:0.00; stir:

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:0.00; pressure:0.00; stir:

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

Procedure: To a solution of 12 g of 7-methoxy-3-methyl-3,4-dihydroisoquinoline in 120 ml of dimethoxyethane was added 16 g of 2'-methyl-2-bromoacetophenone, and the mixture was stirred at room temperature for 14 hours. The resulting white powder was collected by filtration to give 13 g of 7-methoxy-3-methyl-2-(2-methylphenyl)-3,4-dihydroisoquinolinium bromide. A mixture of this white powder, 80 ml of acetic acid and 12.8 g of ammonium acetate was then refluxed for 3 hours. After being cooled, the reaction mixture was poured into water, rendered alkaline by the addition of a saturated sodium carbonate solution and extracted with ethyl acetate. The extract was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel to give 5.3 g of the title compound as a yellow oily material. The resulting white powder was collected by filtration

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

Procedure: A mixture of 3.0 g of 1-aminoisoquinoline, 6.7 g of 2'-methyl-2-bromoacetophenone and 17.5 g of sodium bicarbonate in 50 ml of ethanol was refluxed for 2 hours. After being cooled, the reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and saturated saline, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel and recrystallized from dichloromethane/petroleum ether to give 4.4 g of the title compound as pale brown prisms. was refluxed for 2 hours After being cooled extracted with ethyl acetate The extract was washed with water and saturated saline dried over anhydrous magnesium sulfate The drying agent was removed by filtration the solvent was removed under reduced pressure The residue was purified by column chromatography on silica gel recrystallized from dichloromethane/petroleum ether

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

Procedure: To a solution of 3 g of 2'-methylacetophenone in 60 ml of acetic acid was added successively 9.7 ml of 47% hydrobromic acid and 8.6 g of pyridinium hydrobromide perbromide, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with water and a saturated sodium carbonate solution, and dried over anhydrous magnesium sulfate. The drying agent was removed by filtration, and the solvent was removed under reduced pressure to give 5.4 g of the title compound as a colorless oily material. extracted with ethyl acetate The extract was washed with water a saturated sodium carbonate solution, and dried over anhydrous magnesium sulfate The drying agent was removed by filtration the solvent was removed under reduced pressure

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