Hydrochloric Acid → 6-Chloro-3-methylpyridine-2-carboxylic acid

HRID 1799553Notes

Reaction equation

HRID 1799553 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#N)[C:5]([CH3:10])=[CH:4][CH:3]=1.[OH-:11].[K+].Cl.[OH2:14]>>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([OH:14])=[O:11])[C:5]([CH3:10])=[CH:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14797Potassium HydroxideHCID 468562786-Chloro-3-methylpyridine-2-carbonitrile

Product 1

HCID 469414706-Chloro-3-methylpyridine-2-carboxylic acid

Procedure

6-Chloro-3-methylpyridine-2-carbonitrile (2.95 g, 19.3 mmol) and Potassium hydroxide (3.25 g, 58 mmol) were stirred in refluxing water (60 mL) for 2 hours. The mixture was cooled to room temperature, 30 mL of 2 N HCl was added, followed by the addition of water. The resulting mixture was extracted with EtOAc (3×). The combined organic extracts were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo to give the title compound as a white solid.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×)
  2. washThe combined organic extracts were washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-850c5a3452794c8b902f09a689b2d0bb
Source dataset
uspto-grants-2013_01
Patent number
US08344144B2

Reaction notes

Loading…