Potassium Carbonate → HCID 12812973, compound

HRID 1074620Notes

Reaction equation

HRID 1074620 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][NH:8][C:9]2=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:25][CH2:26][CH2:27][OH:28]>CN(C)C=O>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][N:8]([CH2:25][CH2:26][CH2:27][OH:28])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 12812981HCID 12812981, compound

Product 1

HCID 12812973HCID 12812973, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

25 g of 7-chloro-4-ethoxycarbonyl-1(2H)-isoquinolone was dissolved in 100 ml of dimethylformamide while warming, and 27 g of anhydrous potassium carbonate was added to the solution, followed by stirring for 2 hours at 110° C. Then, 14 g of 3-chloropropanol was added thereto and the stirring was continued for 5 hours at 110° C.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 ethanol and petroleum ether to obtain 20.1 g of 7-chloro-4-ethoxycarbonyl-2-(3-hydroxypropyl)-1-(2H)-isoquinolone having a melting point of 193° C. as colorless prisms.

Workup

  1. temperaturewhile warming
  2. waitthe stirring was continued for 5 hours at 110° C
  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 ethanol and petroleum ether

Sources & evidence

ORD record
ord-13f086f257b841e3be68710007eadcbc
Source dataset
uspto-grants-1983_07
Patent number
US04393210

Reaction notes

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