p-Anisoyl chloride → HCID 67165918, compound

Participants

Reaction Steps

1,2,3,4-Tetrahydro-quinoline-4-carboxylic acid (305 mg, 1.89 mmol) was dissolved in anhydrous tetrahydrofuran (10 mL). Anisoyl chloride (644 mg, 3.78 mmol) was added followed by diisopropylethylamine (733 mg, 1.01 mL, 15.67 mmol). The reaction was stirred at room temperature for 7 days. The mixture was concentrated and partitioned between chloroform and sodium hydroxide (1 M, aqueous). The chloroform extract was set aside. The aqueous phase was acidified with concentrated hydrochloric acid (pH=3-4). The aqueous phase was then extracted with ethyl acetate (three times). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and concentrated. The crude product was used without further purification. MS m/z: 312 (M+1).

Provenance & Evidence