Sodium Azide → Methyl 4-aminopyridine-2-carboxylate

Participants

Reaction Steps

A mixture of 2.0 g of methyl 4-chloropicolinate and 2 g of sodium azide in 20 ml of dimethylformamide is stirred at 100° for 8 hours. The solvent is removed in vacuo, the reaction is diluted with water and the product extracted into ethyl acetate. After drying over magnesium sulfate, the solvent is removed in vacuo. The residue is hydrogenated in 30 ml of ethanol at atmospheric pressure over 500 mg of 10% palladium on carbon catalyst for 3 hours. After filtration through filter-cel the solvent is removed in vacuo and the residue crystallized from ether to afford methyl 4-aminopicolinate.

Provenance & Evidence