Dimethylformamide → 1-Methyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde

Participants

Reaction Steps

To a solution of 1-methyl-1,2,3,4-tetrahydroquinoline (4.4 g, ca. 30.0 mmol) in DMF (30 mL) was added POCl3 (2.8 mL, 30.0 mmol, 1.0 eq) at 0° C. The mixture was allowed to warm to room temperature and stirred overnight. The reaction mixture was poured onto ice then extracted with Et2O (3×50 mL). The combined organic layers were dried over Na2SO4 then concentrated to give a crude product which was purified by flash column chromatography (0-20% EtOAc in hexanes) to afford the title compound (2.17 g, 12.4 mmol, 41% over two steps).

Provenance & Evidence