Perchloric Acid → (RS)-2-(n-pentadecyl)indoline-5-carboxylic acid hydrochloride

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Perchloric acid (3 ml) was added to a hot solution of 2-(n-pentadecyl)indole-5-carboxylic acid in glacial acetic acid (60 ml) and the mixture was hydrogenated at normal pressure using palladium on charcoal (5% w/w, 0.7 g) as catalyst. After 3.5 hours the hot mixture was filtered and the residue was washed with hot glacial acetic acid (30 ml). The pH of the combined filtrates was adjusted to 6 with 10% w/v sodium hydroxide solution. The mixture was extracted with diethyl ether (2×75 ml) and the ether solution was dried over magnesium sulphate. The solution was treated with a saturated solution of hydrogen chloride gas in ethanol to precipitate the hydrochloride. The solid was collected and recrystallised from isopropanol to give (RS)-2-(n-pentadecyl)indoline-5-carboxylic acid hydrochloride (5.6 g) as a white solid, m.p. 165°-170° C. with decomposition.

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