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Indol-1-yl-acetic Acid is a reactant used in the preparation of conformationally restrained analogs of pravadoline; nanomolar potent, enantioselective, (aminoalkyl)?indole agonists of the cannabinoid receptor.

ChEBI: An indolyl carboxylic acid that is acetic acid in which one of the methyl hydrogens is substituted by an indol-1-yl group.

Step 2: Preparation of 2-(1H-indol-1-yl)acetic acid Ethyl 2-(1H-indol-1-yl)acetate (2.03 g, 10 mmol) was dissolved in ethanol (40 mL), aqueous sodium hydroxide solution (1 N, 50 mL) was added, and the reaction was stirred at room temperature for 1.5 hours. Upon completion of the reaction, the reaction solution was adjusted to slightly acidic with dilute hydrochloric acid and the mixture was subsequently concentrated under reduced pressure. The residue was extracted with ethyl acetate and the organic phase was washed with brine and the solvent was removed under reduced pressure to give pure 2-(1H-indol-1-yl)acetic acid (1.6 g, 87% yield), (LC/MS: m/z = 176.3 [M+H]+).

[1] Patent: WO2015/106025, 2015, A1. Location in patent: Paragraph 0334
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