2-CHLORO-5-METHYL-NICOTINIC ACID METHYL ESTER Chemical Properties

Boiling point:

270.1±35.0 °C(Predicted)

Density 

1.247±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

form 

solid

pka

-0.99±0.10(Predicted)

Appearance

White to off-white Solid

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

WGK Germany 

3

HazardClass 

IRRITANT

HS Code 

2933399990

2-CHLORO-5-METHYL-NICOTINIC ACID METHYL ESTER Usage And Synthesis

Synthesis

General procedure for the synthesis of methyl 2-chloro-5-methylnicotinate from methylboronic acid and methyl 5-bromo-2-chloronicotinate: To a toluene solution (16 mL) of methyl 5-bromo-2-chloronicotinate (1.05 g, 4.19 mmol), K3PO4 (2.95 g, 13.90 mmol), methylboronic acid (0.32 g, 5.26 mmol) and tricyclohexylphosphine (0.11 g, 0.39 mmol) in a toluene solution (16 mL) under nitrogen atmosphere, water (0.8 mL) was added followed by Pd(OAc)2 (0.04 g, 0.18 mmol). The mixture was heated at 100 °C under nitrogen atmosphere for overnight reaction. After completion of the reaction, the mixture was cooled to room temperature and concentrated under vacuum. Ethyl acetate was added to the residue and the organic layer was washed sequentially with water and brine, dried with MgSO4, filtered and the solvent was evaporated under vacuum to afford the target product methyl 2-chloro-5-methylnicotinate as a yellow oil in 87% yield.LRMS: m/z 186 (M + 1)+, retention time: 4.84 min.

References

[1] Patent: WO2008/77639, 2008, A1. Location in patent: Page/Page column 26