Hydrochloric Acid → 2-Hydroxy-5-(pyrrolidine-1-sulfonyl)benzoic acid

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Reaction Steps

A solution of 5-chlorosulfonyl-2-hydroxybenzoic acid (0.52 g, 2.0 mmol, Matrix Scientific) in tetrahydrofuran (10 mL) was treated with pyrrolidine (1.5 g, 21 mmol) and refluxed for 2 h. This was cooled and poured into dilute aqueous hydrochloric acid and extracted into dichloromethane (2×50 mL). The combined extracts were washed with brine, dried over magnesium sulfate, filtered, and concentrated to give a solid. This was triturated with ether to give 2-hydroxy-5-(pyrrolidine-1-sulfonyl)benzoic acid as a solid. It was then converted to 2-ethoxy-5-(pyrrolidine-1-sulfonyl)benzoic acid ethyl ester In a manner analogous to the method described in example 33.

Provenance & Evidence