4-(Chloromethyl)pyridinium chloride → N-(2-Hydroxyethyl)-4-pyridinecarboxamide

HRID 2050173Notes

Reaction equation

HRID 2050173 reaction equation
[N+]([O-])(O)=[O:2].[CH2:5]([CH2:7][NH2:8])[OH:6].Cl.[CH2:10](Cl)[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1>O.C(=O)([O-])[O-].[K+].[K+].O1CCCC1>[OH:6][CH2:5][CH2:7][NH:8][C:10](=[O:2])[C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

6

Reactant 2

HCID 745704-(Chloromethyl)pyridinium chlorideHCID 159895(2-Hydroxyethyl)ammonium nitrate

Product 1

HCID 73327N-(2-Hydroxyethyl)-4-pyridinecarboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent2×

Procedure

To a mixture of 1.69 g of the nitric ester of monoethanolamine nitrate in 5 ml of water, 3.8 ml of 35% potassium carbonate solution and 17 ml of tetrahydrofuran were added alternately 3 g of isonicotinyl chloride hydrochloride and 11.2 ml of 35% potassium carbonate aqueous solution over 30 minutes under stirring at 0° to 5° C. The reaction mixture was stirred for an additional 15 minutes, and the organic layer was separated. The aqueous layer was extracted with tetrahydrofuran and the extract was combined with the previously separated organic layer. The combined organic layers were dried over anhydrous sodium sulfate and filtered. Evaporation of the solvent in vacuo and crystallization of the residue afforded the nitric ester of N-(2-hydroxyethyl) isonicotinamide.

Workup

  1. stirringThe reaction mixture was stirred for an additional 15 minutes
  2. customthe organic layer was separated
  3. extractionThe aqueous layer was extracted with tetrahydrofuran
  4. dry with materialThe combined organic layers were dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customEvaporation of the solvent
  7. customin vacuo and crystallization of the residue

Sources & evidence

ORD record
ord-b4200c42d82f4a3ab760f249c8b3fe51
Source dataset
uspto-grants-1980_04
Patent number
US04200640

Reaction notes

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