Hydrochloric Acid → 2-Chloro-4-methylpyridine-3-carboxylic acid

HRID 369457Notes

Reaction equation

HRID 369457 reaction equation
[Cl:1][C:2]1[N:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[C:4]([O:6]CC)=[O:5].[OH-].[Na+].Cl>C(O)C>[Cl:1][C:2]1[N:12]=[CH:11][CH:10]=[C:9]([CH3:13])[C:3]=1[C:4]([OH:6])=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 11769512Ethyl 2-chloro-4-methylnicotinate

Product 1

HCID 154837662-Chloro-4-methylpyridine-3-carboxylic acidYield 79.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 21.8 g (0.109 mole) of ethyl 2-chloro-4-methyl-nicotinate (6) and 55 mL of a 2N-sodium hydroxide solution in 20 mL of ethanol, was refluxed for 8 hours. The solution was acidified with 2N hydrochloric acid and extracted with ether. The organic phase was dried over magnesium sulfate, filtered and concentrated to give 14.8 g (79%) of 2-chloro-4-methylnicotinic acid (7)- as a white solid, mp: 152-154° C., MS (MH)+ 172, NMR (DMSO) ppm: 2.34 (s,3H); 7.39 (d,1H); 8.33 (d,1H); 14.0 (bs COOH).

Workup

  1. temperaturewas refluxed for 8 hours
  2. extractionextracted with ether
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31c173b91c5a4ba49c2d9ab3069c523f
Source dataset
uspto-grants-2000_10
Patent number
US06136982

Reaction notes

Loading…