Sodium Hydroxide → HCID 70984314, compound

Participants

Reaction Steps

2-(3-aminophenyl)acetic acid (11.0 g, 72.8 mmol) was dissolved in 6 N HCl (200 mL) and heated to reflux. (E)-but-2-enal (11.9 mL, 146 mmol) was added dropwise over 10 minutes. The reaction was heated at reflux for 2 hours. After cooling to ambient temperature, the reaction mixture was basified with sodium hydroxide to pH˜12 and ether (100 mL) was added. The aqueous layer was separated, acidified with saturated potassium hydrogen sulfate to pH˜3-4, extracted with 3:1 CHCl3:IPA (3×300 mL), dried (sodium sulfate) and concentrated to give a solid. The solid was dissolved in MeOH (200 mL). The residue was suspended in ethyl acetate (100 mL) and saturated sodium bicarbonate (50 mL). The organic layer was separated, washed with brine, dried (sodium sulfate) and concentrated. The residue obtained was purified by flash chromatography (5:1 DCM:ethyl acetate) to give methyl 2-(2-methylquinolin-7-yl)acetate as a solid.

Provenance & Evidence