Hydrochloric Acid → Methyl 2-chloro-6-(chlorosulfonyl)benzoate

Participants

Reaction Steps

34.6 gm (0.186 mol) of methyl 6-chloro-anthranilate were added to 70 ml of concentrated aqueous hydrochloric acid while stirring and cooling. At 0° to +10° C. the reaction mixture was diazotized with a solution of 12.8 gm (0.186 mol) of sodium nitrite in 30 ml of water. After stirring at 0° C. for 45 minutes, the reaction mixture was poured into a stirred suspension of 2 gm of copper(I) chloride and 17 gm of copper (II)chloride in 160 ml of a 30% solution of sulfur dioxide in glacial acetic acid. After the evolution of nitrogen had ceased, the reaction mixture was stirred for 2 hours at room temperature. After extraction with ether, the organic extracts were washed, dried and evaporated.

Provenance & Evidence