Methanol → Methyl 6-aminonicotinate

Participants

Reaction Steps

6-Aminonicotinic acid (1.06 g, 7.7 mmol) was suspended with stirring in anhydrous methanol (50 ml), and thionyl chloride (0.55 ml, 7.7 mmol) was added dropwise. The suspension was refluxed to a clear solution over 15 hours. The solvent was evaporated in vacuo and the residue taken up in water (20 ml). The solution was raised to pH 9 (sat. Na2CO3), extracted with chloroform, and dried over MgSO4. Evaporation of the chloroform gave 1.23 g (100%) product as white crystals identified by 400 MHz nmr and ir 1694 cm-1.

Provenance & Evidence