Epichlorohydrin → HCID 13187644, compound

HRID 326018Notes

Reaction equation

HRID 326018 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.[CH2:18]([CH:20]1[O:22][CH2:21]1)Cl.[H-].[Na+]>CN(C)C=O>[O:22]1[CH2:21][CH:20]1[CH2:18][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 7835EpichlorohydrinHCID 24758Sodium hydrideHCID 124077244-phenylisoquinolin-1(2H)-one

Product 1

HCID 13187644HCID 13187644, compoundYield 179%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

22 g of 4-phenyl-1(2H)-isoquinolone, 4.1 g of epichlorohydrin and 4.3 g of sodium hydride were added to 500 ml of dimethylformamide, and the mixture was stirred overnight at room temperature. Thereafter, the solvent was distilled off, and chloroform and water were added to the residue. The mixture was thoroughly shaked, and the chloroform layer was separated and dried over magnesium sulfate. The solvent was distilled off, and the residue was recrystallized from ethyl acetate to obtain 22 g (80% yield) of 2-(2,3-epoxypropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 148° C. as colorless needles.

Workup

  1. distillationThereafter, the solvent was distilled off
  2. additionchloroform and water were added to the residue
  3. customthe chloroform layer was separated
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-e3303f5bf5a042ccac6aa730bc9213e6
Source dataset
uspto-grants-1984_04
Patent number
US04443607

Reaction notes

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