Phosphorus oxychloride → Isoquinoline,3,4-dihydro-6-methoxy-

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Reaction Steps

Phosphorus oxychloride (80 mL, 0.85 mol) was added dropwise to N-[2-(3-methoxy-phenyl)-ethyl]-formamide (41.1 g, 0.24 mol) and refluxed for 1 hour. The reaction mixture was cooled to room temperature, and hexane (3×500 mL) was added and decanted off three times. To the dark oily solution was added slowly water (200 mL) while stirring. The mixture was basified with NaOH to pH>13, extracted with ethyl acetate, dried (Na2SO4) and concentrated to afford the desired product (26.1 g, 67%). MS: 162.1 (M+1+).

Provenance & Evidence