Hydrochloric Acid → 2-Bromo-5-methylpyridine-3-carboxylic acid

HRID 848210Notes

Reaction equation

HRID 848210 reaction equation
[Br:1][C:2]1[N:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4]([O:6]CC)=[O:5].Cl>[OH-].[Na+]>[Br:1][C:2]1[N:12]=[CH:11][C:10]([CH3:13])=[CH:9][C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12919731Ethyl 2-bromo-5-methylpyridine-3-carboxylate

Product 1

HCID 129197322-Bromo-5-methylpyridine-3-carboxylic acidYield 89.1%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of ethyl 2-bromo-5-methylnicotinate (7.1 g, 0.03 m) and 10% NaOH solution (500 ml) was heated on a stream bath with stirring. After 3 hours, the solution was cooled and neutralized with 12 N HCl. After cooling in an ice bath, the mixture was filtered to yield 5.6 g (39% yield) of 2-bromo-5-methylnicotinic acid.

Workup

  1. temperaturewas heated on a stream bath
  2. temperaturethe solution was cooled
  3. temperatureAfter cooling in an ice bath
  4. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-6a2dc7bf187d47a59efad72b2698b831
Source dataset
uspto-grants-1981_10
Patent number
US04294969

Reaction notes

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