Thionyl Chloride → Quinoline-3-carbonyl Chloride

HRID 544350Notes

Reaction equation

HRID 544350 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]=[C:7]([C:15]([OH:17])=O)[CH:6]=1>>[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[C:7]([C:15]([Cl:3])=[O:17])[CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 80971Quinoline-3-carboxylic acid

Product 1

HCID 11030631Quinoline-3-carbonyl Chloride

Procedure

A 300 ml eggplant-shaped flask was equipped with a Dimroth condenser, a calcium chloride tube and a dropping funnel, and in the flask, 0.6 mol of thionyl chloride was slowly dropped to 0.1 mol of 3-quinolylcarboxylic acid with stirring at room temperature. After completion of the dropping, the resulting mixture was stirred continuously for about 1 hour on an oil bath at an oil bath temperature of 65° C. Thereafter, the excess thionyl chloride was removed under a reduced pressure to obtain 3-quinolylcarboxylic acid chloride.

Workup

  1. customA 300 ml eggplant-shaped flask was equipped with a Dimroth condenser, a calcium chloride tube and a dropping funnel
  2. stirringAfter completion of the dropping, the resulting mixture was stirred continuously for about 1 hour on an oil bath at an oil bath temperature of 65° C
  3. customThereafter, the excess thionyl chloride was removed under a reduced pressure

Sources & evidence

ORD record
ord-174559f5148f4569b93cf67afeb710e1
Source dataset
uspto-grants-1984_05
Patent number
US04449516

Reaction notes

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