Epichlorohydrin → HCID 13187649, Verbindung

HRID 326019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 326019
[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.[H-].[Na+].[CH2:20]([CH:22]1[O:24][CH2:23]1)Cl.[CH2:25]([NH:27][CH2:28][CH3:29])[CH3:26]>CN(C)C=O>[CH2:25]([N:27]([CH2:28][CH3:29])[CH2:20][CH:22]([OH:24])[CH2:23][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])[CH3:26]

Komponenten

6

Edukt 4

HCID 7835EpichlorohydrinHCID 8021DiethylamineHCID 24758Sodium hydrideHCID 124077244-phenylisoquinolin-1(2H)-one

Produkt 1

HCID 13187649HCID 13187649, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 6.6 g of 4-phenyl-1(2H)-isoquinolone, 2.9 g of 50% sodium hydride and 80 ml of dimethylformamide was stirred at 60° to 70° C. for 3 hours. 5.5 g of epichlorohydrin was then added dropwise to the reaction solution while cooling and stirring, and the mixture was then stirred at room temperature for 12 hours. The reaction solution was poured into ice-water, and the precipitated crystals were collected by filtration and washed with water. The crystals thus obtained were dissolved in 40 ml of dimethylformamide, 12 ml of diethylamine was added thereto and the mixture was heated at 100° C. for 5 hours in a sealed tube. The residue obtained after distilling off the solvent was dissolved in diethyl ether, and the solution was washed with water and extracted with 5% hydrochloric acid. The extract was rendered neutral with 10% aqueous solution of sodium hydroxide to precipitate crystals which were then collected by filtration and recrystallized from a mixture of ethyl acetate and petroleum ether to obtain 6.5 g (61% yield) of 2-(3-diethylamino-2-hydroxypropyl)-4-phenyl-1(2H)-isoquinolone having a melting point of 106° C. as colorless prisms.

Aufarbeitung

  1. temperaturewhile cooling
  2. stirringstirring
  3. stirringthe mixture was then stirred at room temperature for 12 hours
  4. filtrationthe precipitated crystals were collected by filtration
  5. washwashed with water
  6. customThe crystals thus obtained
  7. customThe residue obtained
  8. distillationafter distilling off the solvent
  9. dissolutionwas dissolved in diethyl ether
  10. washthe solution was washed with water
  11. extractionextracted with 5% hydrochloric acid
  12. customto precipitate crystals which
  13. filtrationwere then collected by filtration
  14. customrecrystallized from a mixture of ethyl acetate and petroleum ether

Quellen und Nachweise

ORD-Eintrag
ord-bf3c1e1bb98945a0a26234809f3b5dd8
Quelldatensatz
uspto-grants-1984_04
Patentnummer
US04443607

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