Sodium Hydroxide → Ethyl 4-chloro-7-methoxyquinoline-3-carboxylate

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Reaction Steps

The intermediate from step A (890 mg, mmol) was suspended in POCl3 (5 mL) and refluxed for 1 hour. The reaction was cooled to room temperature and poured into an erlenmeyer flask containing ice and 5 N NaOH (30 mL). The resulting mixture was extracted with ethyl acetate (3×). The organic layer was washed with saturated NaHCO3, saturated NaCl solution dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was purified by flash chromatography using 30% ethyl acetate-hexanes to afford the product as a white solid. 1H NMR (500 MHz, CDCl3): 9.19 (s, 1H), 8.33 (s, J=9.2 Hz, 1H), 7.46 (d, J=2.5 Hz, 1H), 7.36 (dd, J=2.5, 9.1 Hz, 1H), 4.53 (q, J=7.1 Hz, 2H), 4.01 (s, 3H), 1.5 (t, J=7.4 Hz, 3H). LC-MS: 3.22 min; (M+H)=266.1.

Provenance & Evidence