Sodium Hydroxide → 6-Methylphenanthridine

Participants

Reaction Conditions

Reaction Steps

A mixture of the acetamide 4 (717 mg, 3.39 mmol) and finely grinded polyphosphoric acid (10 mL, 115% H3PO4 equiv.) was stirred at 150° C. for 2.5 hours. The reaction mixture was then cooled to 0° C. and slowly basified to pH 14 with saturated NaOH (aq). The mixture was extracted with CH2Cl2 (4×30 mL), and the organic phase dried with MgSO4. Evaporation of the solvent under reduced pressure, followed by flash chromatography over silica, eluting with a gradient of 100% CH2Cl2 to 10% MeOH/90% CH2Cl2, yielded the phenanthridine 5 as a crystalline white solid (567 mg, 86.6%).

Provenance & Evidence