Dichloromethane → HCID 70983733, compound

Participants

Reaction Steps

A solution of 3-amino-2-cyclopropylbenzoic acid (0.507 g, 2.86 mmol) in 6 N HCl (8 mL) was added (E)-but-2-enal (0.47 mL, 5.72 mmol) dropwise at reflux. The reaction mixture was stirred at reflux for 2 hours. After cooling to ambient temperature, the reaction mixture was basified with sodium hydroxide to about pH 12 and DCM (20 mL) was added. The aqueous layer was separated and acidified with saturated potassium hydrogen sulfate to about pH 3-4. The aqueous layer was then extracted with 3:1 CHCl3/IPA (2×30 mL), dried (sodium sulfate), filtered and concentrated under reduced pressure to give 8-cyclopropyl-2-methylquinoline-7-carboxylic acid (0.18 g, 27.7%) as a solid.

Provenance & Evidence