Oxalyl chloride → HCID 21110101, compound

Participants

Reaction Steps

A solution of 6-methoxy-1,2,3,4-tetrahydroquinoline (10 g, 61.3 mmol) 600 mL CH2Cl2 was slowly added to a solution of oxalyl chloride (8.4 mL, 94.5 mmol) in 100 mL CH2Cl2 at 0° C. After addition the reaction mixture was at 0° C. for 0.5 h, aluminum chloride (24.5 g, 184 mmol) was than added to the reaction mixture, the resulting mixture was warmed up to room temperature, stirred over night. The reaction mixture was poured on ice, diluted with 1N HCl, the aqueous layer was extracted with CHCl3 (3×150 mL), the combined organic layers was washed with brine, dried over Na2SO4. The solvent was concentrated, the crude product was purified by flash chromatography (Hexane/EtOAc), obtained 10.0 g (75%) of pure title compound: 1H NMR (300 MHz, CDCl3) 2.01-2.05 (m, 2H), 2.74 (t, 2H, J=6.0 Hz), 3.73 (t, 2H, J=5.8 Hz), 3.77 (s, 3H), 6.92-6.93 (m, 2H).

Provenance & Evidence