Thionyl Chloride → HCID 19860557, compound

HRID 1736551Notes

Reaction equation

HRID 1736551 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([OH:13])=O)[CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:16])=O>ClCCl>[ClH:16].[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]([Cl:16])=[O:13])[CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 665828-Quinolinecarboxylic acid

Product 1

HCID 19860557HCID 19860557, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 8-quinolinecarboxylic acid (10.0 g, 57.8 mmol) in an ice/methanol bath was added thionyl chloride (90.0 ml, 123.4 mmol) in one portion. The reaction mixture was slowly warmed to room temperature and was stirred for 24 hours. Dichloromethane (100 ml) was added and the reaction mixture was refluxed for 1 hour. The solvents were removed by distillation under reduced pressure and the residue was dried for 24 hours at 80° C. in high vacuum to afford 12.6 g (96%) of 8-quinolinecarboxylic acid chloride hydrochloride as a tan powder, m.p. 232°-237° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 1 hour
  2. customThe solvents were removed by distillation under reduced pressure
  3. customthe residue was dried for 24 hours at 80° C. in high vacuum

Sources & evidence

ORD record
ord-21755b31d6364279ac9bf685c90e4b95
Source dataset
uspto-grants-1996_07
Patent number
US05541187

Reaction notes

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