Water → 2-Pyridinecarboxamide

HRID 1077082Notes

Reaction equation

HRID 1077082 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)#[N:2].[OH2:9]>>[N:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[C:1]([NH2:2])=[O:9]

Participants

3

Reactant 2

HCID 962WaterHCID 7522Pyridine-2-carbonitrile

Product 1

HCID 150702-PyridinecarboxamideYield 82%

Procedure

261/2 Grams (0.205 moles) of 2-cyanopyridine, 35 grams of Dowex 1-X8 anion exchange resin (OH- form) and 175 ml. water are placed in a reaction flask fitted with a reflux condenser and magnetic stirrer. After stirring briefly to dissolve the nitrile, the mixture is heated to reflux. After 3 hours and 15 minutes, the resin is filtered off and washed with 100 ml. of boiling water. The combined filtrates are evaporated under reduced pressure, and the resulting solid dried under vacuum at 80°C. An amount of 25.6 grams of picolinamide is obtained, corresponding to an 82% yield based on 2-cyanopyridine. A small amount recrystallized from benzenehexane melts at 107.0°-108.5°C.

Workup

  1. customfitted with a reflux condenser and magnetic stirrer
  2. temperaturethe mixture is heated to reflux
  3. filtration15 minutes, the resin is filtered off
  4. washwashed with 100 ml
  5. customThe combined filtrates are evaporated under reduced pressure
  6. customthe resulting solid dried under vacuum at 80°C

Sources & evidence

ORD record
ord-f6e3fc1532bd4a8db122cf3dee171f39
Source dataset
uspto-grants-1976_05
Patent number
US03959365

Reaction notes

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