2-Bromo-2'-methylacetophenone → HCID 18691251, compound

HRID 376319Notes

Reaction equation

HRID 376319 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 186911993,4-Dihydro-7-methoxy-3-methylisoquinoline

Product 1

HCID 18691251HCID 18691251, compoundYield 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-2025f08458164edb8e4366f1ac3d4753
Source dataset
uspto-grants-2000_02
Patent number
US06020342

Reaction notes

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