2-Pyridinecarboxylic acid, 3-amino-4-cyano-, ethyl ester synthesis
- Product Name:2-Pyridinecarboxylic acid, 3-amino-4-cyano-, ethyl ester
- CAS Number:89241-94-1
- Molecular formula:C9H9N3O2
- Molecular Weight:191.19
Yield:89241-94-1 55%
Reaction Conditions:
with trifluoroacetic acid in 1,2-dichloro-ethane; for 72 h;Reflux;
Steps:
30 Ethyl 3-amino-4-cyanopicolinate
A solution of ethyl 2-cyano-2-formamidoacetate (13.00 g, 83.26 mmol), acrylonitrile (32.9 mL, 499.55 mmol), TFA (6.4 mL, 83 mmol) in 1 ,2-dichloroethane (83 mL) was heated at reflux for 72 h. The reaction was cooled to rt and concentrated under vacuum. The resulting black residue was diluted with DCM (100 mL) and portioned with sat. aq. NaHCO3 (100 mL). The organic layer was collected and the aqueous layer was extracted with DCM (2 x 100 mL). (1054) The combined organic layers were dried (Na2SO4) and concentrated in vacuo onto ISOLUTE HM-N column (Biotage). This was loaded onto an 80 g SiO2 cartridge and eluted with 20 - 50% EtOAc in cyclohexane. Concentration of the product containing fractions afforded the title compound (8.78 g, 55%) as a white solid . 1H NMR (400 MHz, CDCI3) d, ppm 8.12 (1H, d, J= 4.6 Hz), 7.45 (1H, d, J= 4.6 Hz), 6.56 - 6.44 (2H, m), 4.49 (2H, q, J= 7A Hz), 1.46 (3H, t, J= 7.1 Hz).
References:
WO2021/10492,2021,A1 Location in patent:Page/Page column 102-103
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