Ethanolamine → N-(2-hydroxyethyl)nicotinamide

HRID 34899

Reaktionsgleichung

Reaktionsgleichung von HRID 34899
[CH2:1]([CH2:3][NH2:4])[OH:2].[C:5]([O-])(=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[N:8][CH:7]=1.ONC(=O)CCC(N)=O>CN(C)C=O>[OH:2][CH2:1][CH2:3][NH:4][C:5](=[O:12])[C:6]1[CH:11]=[CH:10][CH:9]=[N:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 700EthanolamineHCID 937Nicotinate2×HCID 18381240N-hydroxysuccinamide

Produkt 1

HCID 72663N-(2-hydroxyethyl)nicotinamideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

The ethanolamine was dissolved in dried N,N-di-methyl formamide (DMF) and chilled in an ice bath. The nicotinate derivative, also dissolved in DMF, was added to the DMF-amine mixture, dropwise under a nitrogen atmosphere. As the nicotinate derivative was added, the mixture turned milky and was slurried for at least one half hour. The milky substance was the N-hydroxy-succinamide precipitating, which was filtered off. The DMF-mixture was washed with ether to remove any precipitant. The solvent mixture was removed under high vaccum. The oily residue was triturated with ether, yielding a precipitant, N-(2-hydroxyethyl)-nicotinamide, which was recrystallized from ethyl acetate/petroleum ether. This compound had a melting point of 86°-87° C.; and Rf value of 0.30 (TLC: silica: chloroform/methanol (10:1)); and a yield of 73%.

Aufarbeitung

  1. temperaturechilled in an ice bath
  2. waitwas slurried for at least one half hour
  3. filtrationwas filtered off
  4. washThe DMF-mixture was washed with ether
  5. customto remove any precipitant
  6. customThe solvent mixture was removed under high vaccum
  7. customThe oily residue was triturated with ether

Quellen und Nachweise

ORD-Eintrag
ord-7f0b6dc3b4ec4a73b4593ba147c30853
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04764462

Verknüpfte Notizen

Wird geladen…