Ammonia → 2-Iodo-5-propoxy-benzamide

Participants

Reaction Conditions

Reaction Steps

A mixture of 4.12 g (12.9 mmol) methyl-5-propoxy-2-iodobenzoate and 60 mL MeOH is charged with 129 mL (258 mmol) 2N aq. NaOH solution. The resulting mixture is stirred at 50° C. for 3 h. Then the mixture was acidified to pH5 with 1 M aq. HCl and extracted with EtOAc (2×). The combined organic layers are washed with water and brine, dried with Na2SO4 and the solvent is removed in vacuo. The crude product from the previous saponification is added to 30 mL THF, charged with 2.04 g (12.6 mmol) CDI and stirred at r.t. for 1 h. More 0.5 eq CDI are added and stirring is continued for 20 min. To this mixture are added dropwise 20 mL of 35% ammonia in water and the resulting reaction mixture is stirred at r.t. for 5 min. The solvent is partly removed in vacuo until precipitation of a white solid occurs. The product is filtered and dried at 40° C. in vacuo.

Provenance & Evidence