Ethanol → 3-Ethylisonicotinic acid

HRID 1913757Notes

Reaction equation

HRID 1913757 reaction equation
[CH2:1]([C:3]1[CH:10]=[N:9][CH:8]=[CH:7]C=1C#N)[CH3:2].[OH-:11].[Na+].[CH2:13]([OH:15])[CH3:14]>O>[CH2:1]([C:3]1[CH:10]=[N:9][CH:8]=[CH:7][C:14]=1[C:13]([OH:11])=[O:15])[CH3:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 148632743-Ethylpyridine-4-carbonitrile

Product 1

HCID 450847433-Ethylisonicotinic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.7 g of 3-ethyl isonicotinonitrile, 1.63 g of sodium hydroxide, 20 ml of ethanol and 20 ml of water was heated to reflux for five hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. 3 M hydrochloric acid was added so that pH of the resultant residue became about 3, which was concentrated under reduced pressure again. To the resultant solid, 50 ml of ethanol was added and heated to reflux for five minutes, followed by hot filtration. To the solid collected by filtration, the same operation was carried out by using 50 ml each of ethanol. Combined filtrates were concentrated to give 2.49 g of 3-ethyl isonicotinic acid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for five hours
  3. concentrationconcentrated under reduced pressure
  4. addition3 M hydrochloric acid was added so that pH of the resultant residue
  5. concentrationwas concentrated under reduced pressure again
  6. additionTo the resultant solid, 50 ml of ethanol was added
  7. temperatureheated
  8. temperatureto reflux for five minutes
  9. filtrationfollowed by hot filtration
  10. filtrationTo the solid collected by filtration
  11. concentrationCombined filtrates were concentrated

Sources & evidence

ORD record
ord-5f98025a9f9e472f899c5b3c734a0d34
Source dataset
uspto-grants-2013_12
Patent number
US08609705B2

Reaction notes

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