Carbon Tetrachloride → HCID 12812977, compound

HRID 1074623Notes

Reaction equation

HRID 1074623 reaction equation
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[N:6]([CH2:15][CH2:16]CO)[CH:5]=1)(O)=[O:2].S(Cl)([Cl:21])=O.[C:23]([Cl:27])(Cl)(Cl)Cl>>[Cl:21][C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7](=[O:14])[N:6]([CH2:15][CH2:16][CH2:23][Cl:27])[CH:5]=1)=[O:2]

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 24386Thionyl ChlorideHCID 128129761,2-Dihydro-2-(3-hydroxypropyl)-1-oxo-4-isoquinolinecarboxylic acid

Product 1

HCID 12812977HCID 12812977, compound

Procedure

Then, 12.5 g of 4-carboxy-2-(3-hydroxypropyl)-1(2H)-isoquinolone was added to a mixture of 50 ml of carbon tetrachloride and 25 ml of thionyl chloride, and the resulting mixture was heated at reflux for 2 hours. The solvent was distilled off and the residue was dissolved in dichloromethane. The solution was washed with water, dried and the solvent was distilled off. The resulting crystals were recrystallized from a mixture of ethyl acetate and petroleum ether to obtain 12.8 g of 4-chlorocarbonyl-2-(3-chloropropyl)-1(2H)-isoquinolone having a melting point of 101° C. as colorless prisms.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 2 hours
  3. distillationThe solvent was distilled off
  4. dissolutionthe residue was dissolved in dichloromethane
  5. washThe solution was washed with water
  6. customdried
  7. distillationthe solvent was distilled off
  8. customThe resulting crystals were recrystallized from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-1d3df3cc7f744e4a810163d681a2dec2
Source dataset
uspto-grants-1983_07
Patent number
US04393210

Reaction notes

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