Ethanolamine → N-(2-Hydroxyethyl)picolinamide

HRID 437650Notes

Reaction equation

HRID 437650 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([O:9]C)=O.[NH2:11][CH2:12][CH2:13][OH:14]>>[OH:14][CH2:13][CH2:12][NH:11][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:9]

Participants

3

Reactant 2

HCID 700EthanolamineHCID 755692-Carbomethoxypyridine

Product 1

HCID 2045999N-(2-Hydroxyethyl)picolinamide

Procedure

A mixture of 72 parts of methyl 2-pyridinecarboxylate and 32 parts of 2-aminoethanol is stirred and refluxed carefully for 2 hours. The reaction mixture is cooled and poured onto water. The product is extracted five times with trichloromethane. The combined extracts are dried, filtered and evaporated, yielding 49 parts of N-(2-hydroxyethyl)-2-pyridinecarboxamide as a residue.

Workup

  1. temperaturerefluxed carefully for 2 hours
  2. temperatureThe reaction mixture is cooled
  3. additionpoured onto water
  4. extractionThe product is extracted five times with trichloromethane
  5. customThe combined extracts are dried
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-5704bb8efb124950a0793cacfb9bcc3f
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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