2-Bromo-2'-methylacetophenone → 7-Methoxy-3-methyl-2-(2-methylphenyl)-3,4-dihydroisoquinolinium bromide

HRID 1871465Notes

Reaction equation

HRID 1871465 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([CH3:13])[N:9]=[CH:10]2)=[CH:5][CH:4]=1.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1C(=O)C[Br:23]>C(COC)OC>[Br-:23].[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([CH3:13])[N+:9]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=3[CH3:14])=[CH:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 124306762-Bromo-2'-methylacetophenoneHCID 186911997-Methoxy-3-methyl-3,4-dihydroisoquinoline

Product 1

HCID 186912517-Methoxy-3-methyl-2-(2-methylphenyl)-3,4-dihydroisoquinolinium bromideYield 54.8%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

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.

Workup

  1. filtrationThe resulting white powder was collected by filtration

Sources & evidence

ORD record
ord-7f302400bbfd4f148ed3ed4df8cbb1c1
Source dataset
uspto-grants-2000_08
Patent number
US06103736

Reaction notes

Loading…