Thionyl Chloride → 2-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

HRID 892176Notes

Reaction equation

HRID 892176 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][C:6]=1[CH2:15][O:16][C:17]1[CH:18]=[C:19]([CH2:23]O)[CH:20]=[CH:21][CH:22]=1>ClCCl>[ClH:3].[Cl:3][CH2:23][C:19]1[CH:18]=[C:17]([CH:22]=[CH:21][CH:20]=1)[O:16][CH2:15][C:6]1[CH:7]=[CH:8][C:9]2[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 14650410Benzenemethanol, 3-(2-quinolinylmethoxy)-

Product 1

HCID 145017072-(3-Chloromethylphenoxymethyl)quinoline hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.95 mL, 13 mmol) is added to a solution of [3-(quinolin-2-ylmethoxy)-phenyl]-methanol (2.9 g, 11 mmol, example 48) in dichloromethane (30 mL) and allowed to stir 18 h. The reaction is concentrated in vacuo and azeotroped twice from chloroform to yield the title compound which is used without further purification.

Workup

  1. concentrationThe reaction is concentrated in vacuo
  2. customazeotroped twice from chloroform

Sources & evidence

ORD record
ord-99629d0760534e0bb9d349e9f66ee9a3
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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