Ethanolamine → N-(2-hydroxyethyl)nicotinamide

HRID 703719Notes

Reaction equation

HRID 703719 reaction equation
[C:1]([O:9]CC)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[N:4][CH:3]=1.[CH2:12]([CH2:14][NH2:15])[OH:13]>>[OH:13][CH2:12][CH2:14][NH:15][C:1]([C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1)=[O:9]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 69188Ethyl Nicotinate

Product 1

HCID 72663N-(2-hydroxyethyl)nicotinamideYield 85.1%

Procedure

A solution of 49.2 g (0.32525 mol) ethyl nicotinate and 72 g (1.17 mol) ethanolamine was heated at 70° C. for 60 hours. The excess ethanolamine was removed under reduced pressure and the resulting viscous cream oil was stirred with ether for 48 hours. The resulting white solid was removed by filtration, affording 46 g (85.1%) of the title compound melting at 75°-78° C.

Workup

  1. customThe excess ethanolamine was removed under reduced pressure
  2. customThe resulting white solid was removed by filtration

Sources & evidence

ORD record
ord-818abc6a927948f483fa4d58ce54c7af
Source dataset
uspto-grants-1991_01
Patent number
US04983586

Reaction notes

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