ChemicalBook CAS DataBase List ETHYL 2-CYANOPYRIDINE-3-CARBOXYLATE

ETHYL 2-CYANOPYRIDINE-3-CARBOXYLATE synthesis

5synthesis methods

Product Name:ETHYL 2-CYANOPYRIDINE-3-CARBOXYLATE
CAS Number:75358-90-6
Molecular formula:C9H8N2O2
Molecular Weight:176.17

557-21-1

1452-94-4

75358-90-6

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).

557-21-1 Synthesis

557-21-1
106 suppliers
$12.00/5g

1452-94-4
260 suppliers
$15.00/10g

75358-90-6
69 suppliers
$60.00/50mg

Yield:75358-90-6 100%

Reaction Conditions:

with 1,1'-bis-(diphenylphosphino)ferrocene;zinc;tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ in ISOPROPYLAMIDE at 120; for 1 h;

Steps:

34 Description 34: Ethyl 2-cvanonicotinate

To ethyl 2-chloronicotinate (15.0 g, 81 mmol) in anhydrous N, N-dimethylacetamide (75 ml) was added zinc cyanide (5.71 g, 48.6 mmol), Pd2 (dba) 3 (742 mg, 0.81 mmol), zinc (636 mg, 9.72 mmol), and 1, 1'BIS (diphenylphosphino) ferrocene (898 mg, 1.62 mmol), and the resulting mixture heated at 120 °C for 1 hour. The mixture was cooled to room temperature and partitioned between water (300 ml) and diethyl ether (150 ml), the mixture was filtered through Celiez and the phases separated. The aqueous phase was further extracted with diethyl ether (2 x 100 ml), the combined diethyl ether layers washed with saturated NACI, dried over NA2SO4, FILTERED and evaporated to give the title compound (14.26 g, 100%).

References:

WO2004/46133,2004,A1 Location in patent:Page 31