Ammonia → 2-Iodo-5-propoxy-benzamide

Participants

Reaction Conditions

Reaction Steps

129 mL (258 mmol) 2N NaOH are added to 4.12 g (12.9 mmol) methyl-5-propoxy-2-iodobenzoate (XXVII.1) 60 mL MeOH. The mixture is stirred at 50° C. for 3 h. After that time, the mixture was acidified to pH 5 with 1N aq. HCl and extracted with EtOAc (2×). The combined organic layers are washed with water and brine, dried over sodium sulphate and the solvent is removed in vacuo. The crude product is taken up in 30 mL THF and 2.04 g (12.6 mmol) CDI are added. The mixture is stirred at rt for 1 h. Additional 0.5 eq CDI are added and stirring is continued for 20 min. 20 mL of 35% ammonia in water are added and the resulting mixture is stirred at rt for 5 min. The solvent was partly removed in vacuo until precipitation of a white solid. The product is filtered off and dried at 40° C. in vacuo.

Provenance & Evidence