Thionyl Chloride → 3,7-Dichloroquinolin-8-carbonyl Chloride

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=2[C:13]([OH:15])=O.S(Cl)([Cl:18])=O>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[C:7]([Cl:12])[C:6]=2[C:13]([Cl:18])=[O:15]

Participants

Reactant 2

HCID 24386Thionyl Chloride

HCID 91739Quinclorac

Product 1

HCID 130908403,7-Dichloroquinolin-8-carbonyl ChlorideYield 95.7%

Procedure

3,7-Dichloro-8-quinolinecarboxylic acid(20 g, 82 mmol) was added to thionyl chloride(80 ml), and the mixture refluxed for 3 hours and concentrated under reduced pressure to afford the desired product(20.6 g, yield=95.7%) as a light brown solid.

Workup

temperaturethe mixture refluxed for 3 hours
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-a3d5fd81fa9442d3a1d98dde0c6573c8
Source dataset: uspto-grants-1996_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05489687

Reaction notes

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