Hydrochloric Acid → 4-{[(Benzyloxy)carbonyl]amino}-2-hydroxybenzoic acid

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Reaction Steps

To a solution of sodium-p-aminosalicylate (Aldrich)(100 g, 0.65 mol) in 10% aqueous NaOH solution (1000 ml) is added 50% wt solution of benzylchloroformate (670 g, 1.96 mol in toluene) at 0° C. The resulting mixture is stirred at rt for 48 h. The progression of the reaction is followed by NMR. The reaction mixture is cooled down to 0° C. and acidified with 10% aqueous HCl. The solid obtained is filtered and washed with cold water and dried. It is further treated with petroleum ether and filtered to give crude 4-{[(benzyloxy)carbonyl]amino}-2-hydroxy benzoic acid (128 g, 68%).

Provenance & Evidence