Thionyl Chloride → 4-(Chloromethyl)quinoline--hydrogen chloride (1/1)

Reaction equation

Br.O[CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1.S(Cl)([Cl:16])=O>>[ClH:16].[Cl:16][CH2:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:7]=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 19013536Quinolin-4-ylmethanol hydrobromide

Product 1

HCID 230016194-(Chloromethyl)quinoline--hydrogen chloride (1/1)Yield 80.7%

Procedure

A reaction mixture of 4-(hydroxymethyl)-quinoline hydrobromide (2.0 g, 12.6mmol) and thionylchloride (20 mL) was heated to reflux for 2 hours. This was allowed to cool and then concentrated in vacuum. The green solid was treated with ethyl ether, filtered, washed with ethyl ether and dried in vacuum to yield 4-(chloromethyl)-quinoline hydrochloride (2.17 g, 80.7%).

Workup

temperaturewas heated
temperatureto reflux for 2 hours
temperatureto cool
concentrationconcentrated in vacuum
additionThe green solid was treated with ethyl ether
filtrationfiltered
washwashed with ethyl ether
customdried in vacuum

Sources & evidence

ORD record: ord-9b6a0e8d643b48079adb7a744577a24d
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05331006

Reaction notes

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