Methyl 3-methyl-4-pyridinecarboxylate → 1-Amino-4-(methoxycarbonyl)-3-methylpyridinium 2,4,6-trimethylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

To an ice-cooled suspension (white) of O-(mesitylsulfonyl)hydroxylamine (1.75 g, 8.14 mmol) in dichloromethane (10 ml) is dropwise added a solution of methyl 3-methylisonicotinate (1.23 g, 8.14 mmol) in dichloromethane (3 ml). After the addition is completed, the resulting light yellow solution is stirred for 3 hours at 25° C. The solution is cooled to 0° C. and diluted with diethyl ether until a white solid precipitates. The suspension is stirred for 1 hour and the solid is collected by filtration, washed with ether and dried affording 1-amino-4-(methoxycarbonyl)-3-methylpyridinium 2,4,6-trimethylbenzenesulfonate (2.41 g, 80.8%) as a white solid. MS: m/z=167.2 (M+).

Provenance & Evidence