ETHYL 2-CYANOPYRIDINE-3-CARBOXYLATE Chemical Properties

Melting point:

35-40°C

Boiling point:

185-195 °C(Press: 12 Torr)

Density 

1.21

storage temp. 

2-8°C

pka

-2.25±0.10(Predicted)

form 

solid

Appearance

Off-white to light yellow Solid

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

36/37/39

WGK Germany 

3

HS Code 

2933399990

ETHYL 2-CYANOPYRIDINE-3-CARBOXYLATE Usage And Synthesis

Synthesis

To a solution of ethyl 2-chloropyridine-3-carboxylate (15.0 g, 81 mmol) in anhydrous N,N-dimethylacetamide (75 mL) was added zinc cyanide (5.71 g, 48.6 mmol), tris(dibenzylideneacetone)dipalladium (742 mg, 0.81 mmol), zinc powder (636 mg, 9.72 mmol), and 1,1'-bis(diphenylphosphinyl ) ferrocene (898 mg, 1.62 mmol). The reaction mixture was heated and stirred at 120 °C for 1 hour. After completion of the reaction, the mixture was cooled to room temperature and then partitioned between water (300 mL) and ether (150 mL). The organic and aqueous phases were separated by Celite filtration of the mixture. The aqueous phase was further extracted with ether (2 x 100 mL), all ether layers were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give ethyl 2-cyanonicotinate (14.26 g, 100% yield).

References

[1] Patent: WO2004/46133, 2004, A1. Location in patent: Page 31

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