Ethyl 6-(Aminomethyl)Nicotinate Hydrochloride

White to gray solid

To a solution of ethyl 6-cyano-3-pyridinecarboxylate (3.75 g) and cone. HCl (7.5 mL) in 225 mL ethanol was added 10% Pd/C (wet, 375 mg) and the reaction mixture was hydrogenated using hydrogen balloon and stirred for 12 h. Solution was filtered through celite and ethanol was evaporated to give ethyl 6-(aminomethyl)-3-pyridinecarboxylate HCl as a white solid, which was used in the next step without further purification.[0149] A mixture of 67.2 mL of acetic anhydride and 28.8 mL of formic acid was heated at 50-60 C oil bath temperature for 3 h and then cooled to rt to give formic-acetic anhydride, which was then slowly added into the solid ethyl 2-(aminomethyl)-3-pyridinecarboxylate HCland then stirred at rt for 8 h. Excess reagent was evaporated to give a residue, which was neutralized by very slow addition of sat NaHCC>3 solution. Solution was extracted with DCM, dried and evaporated to provide imidazo[l, 5-a]pyridine as a yellow solid.MS: exact mass calculated for C10H10N2O2, 190.07; m/z found, 191 [M+H] +.

Molecular Weight:216.66
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:4
Exact Mass:216.0665554
Monoisotopic Mass:216.0665554
Topological Polar Surface Area:65.2
Heavy Atom Count:14
Complexity:173
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes