Hydrochloric Acid → 1-Pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarbonitrile (393) (6.2 g, 29.35 mmol) in water (90 mL) was added LiOH.H2O (14 g, 334.56 mmol). The reaction mixture was refluxed for 24 h (TLC, 30% ethyl acetate in hexane, Rf=0.3). It was thereafter cooled to 0° C. and the aqueous part was acidified with HCl (6N) to pH 3 and extracted with ethyl acetate (3×50 mL). The organic phase was thereafter dried and concentrated to get 1-pyrrolo[2,3-b]pyridin-1-yl-cyclopentanecarboxylic acid (394) (5.8 g, 86%) as an off-white solid.

Provenance & Evidence