Ethyl 4-bromo-6-methylpicolinate → 4-Bromo-6-methylpyridine-2-carboxylic acid

HRID 1908819Notes

Reaction equation

HRID 1908819 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[C:10]([Br:12])[CH:9]=[C:8]([CH3:13])[N:7]=1)=[O:5])C>Cl>[Br:12][C:10]1[CH:9]=[C:8]([CH3:13])[N:7]=[C:6]([C:4]([OH:5])=[O:3])[CH:11]=1

Participants

3

Reactant 1

HCID 25208981Ethyl 4-bromo-6-methylpicolinate

Product 1

HCID 534852954-Bromo-6-methylpyridine-2-carboxylic acidYield 116.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 4-bromo-6-methyl-pyridine-2-carboxylic acid ethyl ester (2.42 g, 9.91 mmol) in 6 N aq. HCl (100 mL) is stirred at 65° C. for 18 h. The solvent is evaporated and the residue is dried under HV, suspended in DCM, filtered and dried again under HV to give 4-bromo-6-methyl-pyridine-2-carboxylic acid (2.50 g) as a hydrochloride salt in form of a white powder; LC-MS: tR=0.46 min, [M+1]+=215.93.

Workup

  1. customThe solvent is evaporated
  2. customthe residue is dried under HV
  3. filtrationfiltered
  4. customdried again under HV

Sources & evidence

ORD record
ord-44c781d11a4f445db4019b734588c1a5
Source dataset
uspto-grants-2013_12
Patent number
US08598208B2

Reaction notes

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