Phosphorus oxychloride → 6-Methoxy-1-methyl-3,4-dihydroisoquinoline

Participants

Reaction Steps

To a stirred solution of N-acetyl-3-methoxyphenethylamine (96.0 g, 0.497 m) in toluene (600 ml) at 15°-20° C. phosphorus oxychloride (190.5 g, 1.24 m) was added dropwise over 2 hours. The reaction was stirred overnight at room temperature, then poured into 1 liter of ice water. The organic layer was washed with dilute HCl (2×300 ml), and the aqueous layers were combined, basified, and extracted with CHCl3 (2×500 ml). The dried chloroform layer (MgSO4) was concentrated to an oil. The oil was dissolved in ether and acidified with HCl gas to yield 55.9 g of the product, 3,4-dihydro-6-methoxy-1-methylisoquinoline, m.p. 206°-207°.

Provenance & Evidence