Tetrahydrofuran → 7-(Hydroxyamino)-1-(methoxymethyl)-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

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Reaction Steps

A mixture of 33 g. (0.1 mol) of 1,3-dihydro-1-methoxymethyl-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one, 1 l. of tetrahydrofuran, 1 l. of methanol. 113 g. (0.5 mol) of stannous chloride dihydrate and 136 g. (1 mol) of sodium acetate trihydrate was stirred at room temperature for 6 hrs. under an atmosphere of nitrogen. The inorganic salts were separated by filtration over celite. The filtrate was evaporated and the residue was partitioned between methylene chloride and 1N sodium hydroxide solution. The methylene chloride layer was washed with water, dried and evaporated. Crystallization of the residue from methylene chloride/ether yielded light yellow product with m.p. 168°-170°. For analysis it was recrystallized from the same solvents, m.p. 168°-171°.

Provenance & Evidence