Sulfuric Acid → HCID 66882333, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-chloro-3-methyl-5-(2,2,2-trichloro-ethyl)quinoline (4.11 g, 13.3 mmol) in anhydrous methanol (35 mL) was added a 30% solution of NaOMe in methanol (10.7 mL) under an argon atmosphere. The resulting brown solution was heated for 4 h at 70° C. After cooling to 0° C., concentrated H2SO4 (7 mL) was carefully added and the resulting reaction mixture was heated for 1 h at 70° C. After cooling the reaction mixture was rendered basic (pH=9) with a saturated aqueous NaHCO3 solution and extracted three times with TBDM. The combined organic layers were dried over Na2SO4, filtered and concentrated at reduced pressure to afford a brown solid. Purification by flash column chromatography (silica gel, gradient of cyclohexane/EtOAc 100:0 to 80:20) afforded the title compound as a white powder (2.22 g, 8.90 mmol, 67%). 1H NMR (400 MHz, CDCl3, 298 K): δ=8.80 (s, 1H), 8.09 (s, 1H), 8.05 (d, J=9.2 Hz, 1H), 7.69 (d, J=9.2 Hz, 1H), 4.29 (s, 2H), 3.73 (s, 3H), 2.59 (s, 3H). MS (ES+): 250 (M(C13H1235ClNO2)+H)+.

Provenance & Evidence