Diazomethane → Methyl 2-chloronicotinate

Participants

Reaction Steps

To a cold diethyl ether solution containing about 2.8 g. (0.067 mole) of diazomethane generated from 10 g. of nitrosomethyl urea and 30 cc. of 40% potassium hydroxide (see Organic Synthesis, Col. 1, Vol. II, page 166) was added in portions 9.45 g. (0.06 mole) of 2-chloronicotinic acid. After the evolution of nitrogen had ceased the reaction mixture was allowed to stand at room temperature overnight. The solvent was removed in a rotary evaporator leaving 2-chloro-nicotinic acid, methyl ester as a residual oil whose infrared spectrum indicated no OH absorption was present. The oil was used directly in the next step. The above compound has also been described by F. G. Mann and J. A. Reid, J. Chem. Soc., 1952, 2057.

Provenance & Evidence