4-Quinolinecarboxylic acid → Quinoline-4-carbonyl chloride hydrochloride

HRID 487256Notes

Reaction equation

HRID 487256 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([OH:13])=O)=[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][CH:9]=2)[C:4]([C:11]([Cl:16])=[O:13])=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 102434-Quinolinecarboxylic acidHCID 24386Thionyl Chloride

Product 1

HCID 12373997Quinoline-4-carbonyl chloride hydrochlorideYield 87.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-quinolinecarboxylic acid (5.0 g, 29.1 mmol) at 0° C. under argon was added thionyl chloride (20.0 ml, 0.27 mol). The reaction mixture was slowly warmed to room temperature and stirred for 1 hour. Dichloromethane (100 ml) was added and the reaction mixture was refluxed for 3 hours. The solvents were removed by distillation and the residue was dried at 130° C. in high vacuum to afford 5.8 g (87%) of 4-quinolinecarboxylic acid chloride hydrochloride as a green crystals, m.p. 249°-251° C.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customThe solvents were removed by distillation
  3. customthe residue was dried at 130° C. in high vacuum

Sources & evidence

ORD record
ord-eab098dd9f364caabb6fbc46b3982629
Source dataset
uspto-grants-1994_03
Patent number
US05294612

Reaction notes

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