Thionyl Chloride → 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarbonyl chloride

HRID 1290885Notes

Reaction equation

HRID 1290885 reaction equation
[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:14](O)=[O:15])[C:5]1=[O:17])([CH3:3])[CH3:2].S(Cl)([Cl:20])=O>C1(C)C=CC=CC=1>[CH:1]([N:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]([C:14]([Cl:20])=[O:15])[C:5]1=[O:17])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 109442901-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid

Product 1

HCID 154686831-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarbonyl chloride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3.88 g of 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid and 5.0 ml of thionyl chloride in 50 ml of toluene was stirred at 100° C. for 5 hours. After toluene was distilled off under vacuum, toluene was again added to the residue. The solvent was again distilled off under vacuum to give 4.22 g of 1-isopropyl-2-oxo-1,2-dihydro-3-quinolinecarbonyl chloride.

Workup

  1. distillationAfter toluene was distilled off under vacuum, toluene
  2. additionwas again added to the residue
  3. distillationThe solvent was again distilled off under vacuum

Sources & evidence

ORD record
ord-bf647cf64f954d1f9bfdaef159ac3392
Source dataset
uspto-grants-1998_05
Patent number
US05753673

Reaction notes

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