Methyl 3-amino-4-hydroxybenzoate → 3-(5-Chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester

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Reaction Steps

5-Chloro-2-methoxybenzenesulfonyl chloride (5.77 g, 2.39 mmol) was added to a solution of 3-amino-4-hydroxy-benzoic acid methyl ester (example 1, step 1; 4.00 g, 23.9 mmol) in pyridine (38 mL). The homogeneous solution was stirred at room temperature for 72 h, then partitioned between ethyl acetate and 2 M aq. hydrochloric acid solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. The residue was triturated in ethyl acetate to furnish 3-(5-chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester (7.19 g, 81%). Pink solid, MS (ISP)=370.0 (M−H)−.

Provenance & Evidence