Ethanolamine → N-(2-Hydroxyethyl)picolinamide

HRID 34950

Reaction equation

HRID 34950 reaction equation
[CH2:1]([CH2:3][NH2:4])[OH:2].[N:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11](Cl)=[O:12]>CN(C)C=O>[OH:2][CH2:1][CH2:3][NH:4][C:11]([C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][N:5]=1)=[O:12]

Participants

4

Reactant 2

HCID 700EthanolamineHCID 135034Pyridine-2-carbonyl chloride

Product 1

HCID 2045999N-(2-Hydroxyethyl)picolinamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

15.4 ml of ethanolamine were placed under argon with 30 ml of dimethylformamide and cooled to 0°-5°. A solution of 11.3 g of picolinic acid chloride in 100 ml of dimethylformamide was added dropwise thereto at 0°-10° and the mixture was stirred at room temperature overnight. The dimethylformamide was distilled off under reduced pressure. The residue was dissolved in methylene chloride and separated from the insoluble constituents, and thereafter chromatographed on silica gel; elution agent: methylene chloride, thereafter methylene chloride/methanol (9:1). N-(2-Hydroxyethyl)pyridine-2-carboxamide was obtained as a yellow oil.

Workup

  1. temperaturecooled to 0°-5°
  2. distillationThe dimethylformamide was distilled off under reduced pressure
  3. dissolutionThe residue was dissolved in methylene chloride
  4. customseparated from the insoluble constituents
  5. customchromatographed on silica gel
  6. washelution agent

Sources & evidence

ORD record
ord-73ec8076ef72413595d304b362e40316
Source dataset
uspto-grants-1988_08
Patent number
US04764522

Linked notes

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