Hydrochloric Acid → 6-(benzyloxy)-1H-indole-2-carboxylic acid

Participants

Reaction Steps

Methyl 6-benzyloxyindole-2-carboxylate (EXAMPLE 247, 3.77 g) is dissolved in 33.5 ml of dioxane and 3.35 ml of water is added. Then solid potassium hydroxide (0.9 g) is added and the reaction is heated to 50° for 6 hr. Then a further 0.9 g of potassium hydroxide is added and the reaction is stirred at 20°-25° for 72 hr and heated at 50° a further 4 hr. Then it is cooled to 20°-25° and acidified to pH 4-5 with 2N hydrochloric acid. The reaction is extracted with methanol/chloroform (10/90, 3 times) and the extracts are dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo to provide the title compound.

Provenance & Evidence