Diethyl Ether → 1-Amino-2-(2-chloro-4-methoxyphenyl)-3-methylpyridinium 2,4,6-trimethylbenzenesulfonate

Participants

Reaction Conditions

Reaction Steps

A 0° C. solution of ethyl O-mesitylsulfonylacetohydroxamate (4.68 g, 16.4 mmol) in dioxane (10 mL) was treated with HClO4 (1.8 mL, 20.8 mmol) dropwise over 25 minutes. The reaction was stirred at 0° C. for two hours then poured into ice H2O and stirred vigorously for 30 minutes. The mixture was filtered and the filter cake dissolved in CH2Cl2. The CH2Cl2 solution was washed with cold H2O and passed through a plug of anhydrous K2CO3 directly into a flask containing a 0° C. solution of 2-(2-chloro-4-methoxyphenyl)-3-methylpyridine (1.37 g, 5.9 mmol) in CH2Cl2 (15 mL). The reaction was allowed to stir overnight at room temperature. Diethyl ether was added to the reaction and it was concentrated in vacuo to give a white foam (3.66 g) which was used as is in the next step: MS m/z 249.16 (M++H).

Provenance & Evidence