Diethyl Ether → (4,4'-Dimethoxydesyl)isoquinolinium bromide

HRID 258997Notes

Reaction equation

HRID 258997 reaction equation
[Br:1][CH:2]([C:13]1[CH:20]=[CH:19][C:16]([O:17][CH3:18])=[CH:15][CH:14]=1)[C:3](=[O:12])[C:4]1[CH:11]=[CH:10][C:7]([O:8][CH3:9])=[CH:6][CH:5]=1.CCOCC.[CH:26]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:29]=[CH:28][N:27]=1>C(Cl)(Cl)Cl>[Br-:1].[CH3:9][O:8][C:7]1[CH:10]=[CH:11][C:4]([C:3]([CH:2]([C:26]2[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[CH:29]=[CH:28][NH+:27]=2)[C:13]2[CH:20]=[CH:19][C:16]([O:17][CH3:18])=[CH:15][CH:14]=2)=[O:12])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8405IsoquinolineHCID 3441532-Bromo-1,2-bis(4-methoxyphenyl)ethanone

Product 1

HCID 86734931(4,4'-Dimethoxydesyl)isoquinolinium bromide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A solution of α-bromodeoxy-p-anisoin (12 g) in isoquinoline (12 g) was heated in an oil bath at 160°0 for 10 minutes. The cooled reaction mixture was taken up in chloroform (50 ml), and the chloroform solution added dropwise, with stirring, to ether (600 ml). The suspension was stirred for 30 minutes, and the solid filtered off, washed well with ether and dried. Yield 18.0 g.

Workup

  1. customThe cooled reaction mixture
  2. filtrationthe solid filtered off
  3. washwashed well with ether
  4. customdried

Sources & evidence

ORD record
ord-f93a95240f0346adaa6dc4f89c5e07ca
Source dataset
uspto-grants-1977_07
Patent number
US04035499

Reaction notes

Loading…