1-Acetylnaphthalene → Win 551212 mesylate

Participants

Reaction Steps

Following a procedure similar to that described in Example 2A above, (+)-3-(4-morpholinylmethyl)-5-methyl-6-(1-naphthylcarbonyl)-2,3-dihydropyrrolo[1,2,3-de]-1,4-benzoxazine methanesulfonate (11.6 g from methanol/diethyl ether), m.p. 256°-259° C., [α]D25 =+40 2° (1% in DMF) was prepared by reaction of 15.5 g (0.062 mole) of (+)-3-(4-morpholinylmethyl)-4-amino-3,4-dihydro-2H-1,4-benzoxazine with 15.8 g (0.075 mole) of 4-(1-naphthyl)-2,4-butanedione in 500 ml of toluene in the presence of a catalytic amount of pyridine 3-nitrobenzenesulfonate (the 2,4-diketone being prepared by reaction of methyl 1-naphthyl ketone with ethyl acetate in the presence of sodium hydride and ethanol in diethyl ether), followed by cyclization of the resulting hydrazone by refluxing the latter in 300 ml of glacial acetic acid and recrystallization of the product from methanol/diethyl ether.

Provenance & Evidence