Sodium Hydroxide → 6-methoxy-3,4-dihydroisoquinolin-1(2H)-one

Participants

Reaction Steps

5-Methoxy-1-indanone 1 (30 g, 185 mmol) is dissolved in CH3SO3H (96 mL) and CH2Cl2 (100 mL), NaN3 (24 g, 370 mmol) is then added in portions over a 1/2 hour period. After 2 hours the reaction mixture is cooled to 0° and is subsequently neutralized with 5N NaOH solution (200 mL) and saturated NaHCO3 solution. The resulting mixture is extracted with EtOAc (3×200 mL). The combined organic phases are washed with saturated NaCl solution (3×200 mL), dried over Na2SO4 and concentrated in vacuo. The resulting brown solid is washed with hexanes (2×100 mL) to give 6-methoxy-1-oxo-1,2,3,4-tetrahydroisoquinoline as a tan solid, m.p. 128°-130°.

Provenance & Evidence