Ethanolamine → N-(2-hydroxyethyl)nicotinamide

HRID 1494175Notes

Reaction equation

HRID 1494175 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-560e9f5520d74ab1aba088b916ca2e98
Source dataset
uspto-grants-1991_06
Patent number
US05024998

Reaction notes

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