Thionyl Chloride → HCID 178521120, compound

HRID 1585151Notes

Reaction equation

HRID 1585151 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([C:12]([OH:14])=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.S(Cl)([Cl:17])=O>>[OH:1][C:2]1[CH:11]=[C:10]([C:12]([Cl:17])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178524625HCID 178524625, compound

Product 1

HCID 178521120HCID 178521120, compound

Procedure

A mixture of 2-hydroxyquinoline-4-carboxylic acid (V, 2.89 g) and of thionyl chloride (25 ml) is stirred at 80° for 12 hr and then allowed to cool. Excess thionyl chloride is removed under reduced pressure and dichloromethane is added to the residue. The dichloromethane is then removed and the process repeated to remove traces of thionyl chloride. The residue is dried under reduced pressure to give 2-hydroxyquinolin-4-oyl chloride (V-A) as a solid, which is used without further purification, mp: shrinkage and melting from approximately 260-275°.

Workup

  1. temperatureto cool
  2. customExcess thionyl chloride is removed under reduced pressure and dichloromethane
  3. additionis added to the residue
  4. customThe dichloromethane is then removed
  5. customto remove traces of thionyl chloride
  6. customThe residue is dried under reduced pressure

Sources & evidence

ORD record
ord-ef2da7bbd6504abf82fc75b77b1c8444
Source dataset
uspto-grants-1999_08
Patent number
US05935970

Reaction notes

Loading…