Ethanolamine → N-(2-hydroxyethyl)nicotinamide

HRID 34899

반응식

HRID 34899 반응식
[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

참가 물질

5

반응물 3

HCID 700EthanolamineHCID 937Nicotinate2회HCID 18381240N-hydroxysuccinamide

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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%.

후처리

  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

출처 및 근거

ORD 기록
ord-7f0b6dc3b4ec4a73b4593ba147c30853
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04764462

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