Potassium Carbonate → HCID 12812964, compound

HRID 1074615Notes

Reaction equation

HRID 1074615 reaction equation
[C:1]1([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10](=[O:17])[NH:9][CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:25][CH2:26][CH2:27][OH:28]>CN(C)C=O>[OH:28][CH2:27][CH2:26][CH2:25][N:9]1[CH:8]=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:17]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 123133-Chloro-1-propanolHCID 124077244-phenylisoquinolin-1(2H)-one

Product 1

HCID 12812964HCID 12812964, compoundYield 82.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 22.1 g of 4-phenyl-1(2H)-isoquinolone, 20 g of anhydrous potassium carbonate and 100 ml of dimethylformamide was stirred for 2 hours at 100° C. Then, 11 g of 3-chloropropanol was added to the resulting solution and the mixture was stirred at 110° C. for 5 hours. After completion of the reaction, the solvent was distilled off, and the residue was dissolved in dichloromethane. Water was added to the resulting solution and, after thoroughly stirring, the dichloromethane layer was separated and dried over anhydrous sodium sulfate. The solvent was distilled off, and the resulting residue was recrystallized from a mixture of ethyl acetate and petroleum ether to obtain 23 g of 2-(3-hydroxypropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 84° C. as colorless prisms.

Workup

  1. stirringthe mixture was stirred at 110° C. for 5 hours
  2. customAfter completion of the reaction
  3. distillationthe solvent was distilled off
  4. dissolutionthe residue was dissolved in dichloromethane
  5. additionWater was added to the resulting solution
  6. stirringafter thoroughly stirring
  7. customthe dichloromethane layer was separated
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customthe resulting residue was recrystallized from a mixture of ethyl acetate and petroleum ether

Sources & evidence

ORD record
ord-f34bba894b5d4983aad0bf4b6a287300
Source dataset
uspto-grants-1983_07
Patent number
US04393210

Reaction notes

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