Hydrochloric Acid → 6-Chloro-5-methyl-1-(3-methyl-5-isoxazolylcarbamoyl)indoline

Participants

Reaction Conditions

Reaction Steps

A solution of 3-amino-5-methyl-isoxazole (0.23 g, 2.4 mmol) in N,N-dimethylformamide (4 ml) was treated at 0° C. with sodium hydride (70 mg of 80% dispersion; 2.4 mmol). After 0.25 h the mixture was added dropwise to a solution of carbonyl diimidazole (0.41 g, 2.5 mmol) in N,N-dimethylformamide (4 ml), and after 5 mins the resulting solution was added to a solution of 6chloro-5-methyl indoline (D10) (0.36 g, 2.2 mmol) in N,N-dimethylformamide (4 ml). The mixture was heated at 100° C. for 1 h, allowed to cool to room temperature, then treated with 0.1M aqueous hydrochloric acid (30 ml). Filtration and drying afforded a brown solid (0.5 g). Recrystallisation from ethanol gave the title compound as a white solid (0.40 g, 64%) m.p. >220° C.,

Provenance & Evidence