Ethanol → 2-(Propan-2-yl)pyridine-4-carboxylic acid

HRID 1838250Notes

Reaction equation

HRID 1838250 reaction equation
[OH-:1].[K+].[CH2:3]([OH:5])[CH3:4].C(C1[CH:13]=[CH:12][N:11]=[C:10]([CH:14]([CH3:16])[CH3:15])[CH:9]=1)#N.O>C(OCC)C>[CH:14]([C:10]1[CH:9]=[C:4]([CH:13]=[CH:12][N:11]=1)[C:3]([OH:1])=[O:5])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 14797Potassium HydroxideHCID 1184982-(Isopropyl)isonicotinonitrile

Product 1

HCID 225077152-(Propan-2-yl)pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A 7.5 ml portion of 8 N aqueous potassium hydroxide was added to 50 ml of ethanol solution containing 2.7 g of 4-cyano-2-isopropylpyridine, and the mixture was heated under reflux for 12 hours. After cooling to room temperature, the reaction mixture was mixed with water and diethyl ether and the aqueous layer was separated. The aqueous layer was adjusted to an acidic pH of 3 using 4 N hydrochloric acid and then saturated with sodium chloride. This was extracted with a mixed solvent of ethyl acetate-isopropanol (5:1, v/v) and dried over anhydrous magnesium sulfate, and then the solvent was evaporated under reduced pressure to obtain 3.1 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. customthe aqueous layer was separated
  4. extractionThis was extracted with a mixed solvent of ethyl acetate-isopropanol (5:1
  5. dry with materialv/v) and dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ba4adcc6219246b7ac21553354cbd458
Source dataset
uspto-grants-2004_01
Patent number
US06673799B1

Reaction notes

Loading…