Potassium Carbonate → 2-(2-hydroxypropyl)-4-phenyl-1(2H)-isoquinolone

HRID 326016Notes

Reaction equation

HRID 326016 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][CH:26]([OH:28])[CH3:27]>CN(C)C=O>[OH:28][CH:26]([CH3:27])[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 313701-Chloro-2-propanolHCID 124077244-phenylisoquinolin-1(2H)-one

Product 1

HCID 131876422-(2-hydroxypropyl)-4-phenyl-1(2H)-isoquinoloneYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

44.2 g of 4-phenyl-1(2H)-isoquinolone and 55.2 g of potassium carbonate were mixed with 250 ml of dimethylformamide, and the mixture was heated at 110° C. to 120° C. for 2 hours. Thereafter, 35 g of 70% 1-chloro-2-propanol was added dropwise to the mixture, and then the resulting mixture was stirred and heated for 5 hours. After allowing the mixture to cool, the reaction mixture was poured into ice-water, and the precipitated crystals were collected by filtration, washed with water and then dried. The crystals were recrystallized from a mixture of methanol and diethyl ether to obtain 45.2 g (81% yield) of 2-(2-hydroxypropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 162° C. as colorless needles.

Workup

  1. temperaturethe mixture was heated at 110° C. to 120° C. for 2 hours
  2. temperatureheated for 5 hours
  3. temperatureto cool
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water
  6. customdried
  7. customThe crystals were recrystallized from a mixture of methanol and diethyl ether

Sources & evidence

ORD record
ord-52f47a4017d840308de46bf57811c55c
Source dataset
uspto-grants-1984_04
Patent number
US04443607

Reaction notes

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