Hydrochloric Acid → Ethyl 6-chloropicolinate

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([OH:10])=[O:9])[N:3]=1.Cl.[CH2:12](O)[CH3:13]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([O:10][CH2:12][CH3:13])=[O:9])[N:3]=1

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 702Ethanol

HCID 208126-Chloropicolinic acid

Product 1

HCID 11063114Ethyl 6-chloropicolinate

Procedure

14.1 g (0.0895 mole) of 2-chloro-6-hydroxycarbonylpyridine in 133 ml of a solution of HCl in ethanol is heated for 8 hours under reflux. The solvent is evaporated off, ethyl acetate added and the mixture washed with a solution of bicarbonate. The solvent is further evaporated and the reaction product purified by flash chromatography (cyclohexane/ethyl acetate=7/3). The required product is obtained.

Workup

temperatureunder reflux
customThe solvent is evaporated off
additionethyl acetate added
washthe mixture washed with a solution of bicarbonate
customThe solvent is further evaporated
customthe reaction product purified by flash chromatography (cyclohexane/ethyl acetate=7/3)

Sources & evidence

ORD record: ord-862cce06f01145b7962a2921dbe2c91c
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06649627B1

Reaction notes

Loading…