Methyl p-toluenesulfonate → 1,1-Dimethyl-1,2,3,4-tetrahydro-2-hydroxymethylquinolinium p-toluenesulfonate

HRID 2081501Notes

Reaction equation

HRID 2081501 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:12][OH:13].[C:14]1([CH3:25])[CH:19]=[CH:18][C:17]([S:20]([O:23]C)(=[O:22])=[O:21])=[CH:16][CH:15]=1>>[C:14]1([CH3:25])[CH:15]=[CH:16][C:17]([S:20]([O-:23])(=[O:21])=[O:22])=[CH:18][CH:19]=1.[CH3:1][N+:2]1([CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5][CH2:4][CH:3]1[CH2:12][OH:13]

Participants

3

Reactant 2

HCID 6645Methyl p-toluenesulfonateHCID 124157581-Methyl-1,2,3,4-tetrahydro-2-quinolinemethanol

Product 1

HCID 150522411,1-Dimethyl-1,2,3,4-tetrahydro-2-hydroxymethylquinolinium p-toluenesulfonateYield 202%

Conditions

Temperature
100 °C

Procedure

A mixture of 1.3 g of 1-methyl-1,2,3,4-tetrahydro-2-quinolinemethanol and 1.37 g of methyl p-toluenesulfonate was heated at 100° C. for 6 hours. The solvent was removed from the reaction mixture by decantation, and the residue was washed with ether to give 2.7 g of the desired compound as a dark red oil.

Workup

  1. customThe solvent was removed from the reaction mixture by decantation
  2. washthe residue was washed with ether

Sources & evidence

ORD record
ord-57aab7aa79b9419383473f8bf96381bd
Source dataset
uspto-grants-1993_02
Patent number
US05183811

Reaction notes

Loading…