Hydrochloric Acid → 7-Hydroxy-3,4-dihydrocarbostyril

Participants

Reaction Conditions

Reaction Steps

Under nitrogen with outlet to back of hood, added 12.37 g of aluminum chloride powder (0.093 mol) to 7.93 g of 3-Chloro-N-(3-methoxy-phenyl)-propionamide (0.037 mol). Placed in preheated 160° C. sand bath, and heated for 4 hours, raising bath temperature to 200° C., until no more HCl is observed. Cooled to room temperature, chilled in ice bath and cautiously added ice-H2O. Extracted three times with EtOAc, dried (MgSO4), and evaporated under reduced pressure. Purified by flash chromatography on 230–400 Å mesh silica gel, eluting with 1:1 EtOAc/Hexanes to give 3.3 g of beige solid (55%). 1H NMR (400 MHz, CDCl3) δ 2.60 (2H, q, J=6.23 Hz), 2.88 (2H, t, J=6.85 Hz), 6.23 (1H, d, J=2.49 Hz), 6.44 (1H, q, J=2.49 Hz), 7.00 (1H, d, J=8.09 Hz). M/z (APCI+) 163.7 (M+1).

Provenance & Evidence