Perchloric Acid → HCID 12799980, compound

Participants

Reaction Steps

Methyl 3-(n-octadecanoyl)indole-5-carboxylate (17.30 g) was suspended in glacial acetic acid (400 ml), containing perchloric acid (11 ml, 70% w/v), and was hydrogenated over palladium on charcoal (5% w/w, 15 g) at atmospheric pressure and at a temperature of 80°-90° C. The mixture was then hot filtered through diatomaceous earth and was poured into water (150 ml) to give an off-white solid. The solid was collected, washed with water (2×100 ml) and was dissolved in ethyl acetate (1000 ml). The ethyl acetate solution was washed with an aqueous solution of sodium carbonate (of strength 2N, 150 ml) and the organic layer was separated and was dried over magnesium sulfate. The organic solvent was removed in vacuo to give (RS)-methyl 3-(n-octadecyl)indoline-5-carboxylate in the form of an off-white solid, which was used without purification.

Provenance & Evidence