alpha-Chloro-m-nitrotoluene → 9-(3-Nitrobenzyl)-2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one

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Reaction Steps

A solution of 2,3,9,10a-tetrahydrobenzo[b]cyclopenta[e][1,4]diazepin-10(1H)-one (4.00 g, 20 mmol) in DMF (40 mL) was cooled to 0° C. and sodium hydride (a 60% dispersion in liquid paraffin, 0.80 g, 20 mmol) was added. This mixture was stirred at the same temperature for 20 minutes. To the resulting solution was added 3-nitrobenzyl chloride (3.77 g, 22 mmol) and the mixture was stirred at room temperature for 20 minutes. This reaction mixture was poured in saturated aqueous ammonium chloride solution (40 mL) and extracted with 3 portions of ethyl acetate. The pooled organic layer was washed with water and saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate (MgSO4), filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate-diisopropyl ether to provide 4.81 g (yield 71%) of the title compound. m.p. 123.5°-125.5° C.

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