Acetone → 7-Chloro-1-(2,3-dihydroxypropyl)-5-(o-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one

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Reaction Steps

33.0 g of 1-allyl-7-chloro-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one are dissolved in 300 ml of acetone. 16 g of potassium permanganate are dissolved in 300 ml of a buffer solution (sodium acetate/acetic acid buffer) and added dropwise at 10°C within 20 minutes and with stirring to the foregoing solution. After complete decolouration of the potassium permanganate solution, the mixture is filtered off under vacuum from the manganese dioxide, the manganese dioxide is washed with acetone and the residue is extensively freed from acetone on a rotary evaporator. The remaining aqueous solution is treated with equal portions of methanol, toluene and cyclohexane and partitioned by stirring well. The aqueous/ methanolic phase is then extensively freed from methanol on a rotary evaporator and the remaining aqueous phase is extracted with ethyl acetate. The ethyl acetate solution is washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated. The residue is brought to crystallization by seeding from a small amount of ethyl acetate. By recrystallization of the first crystalline product from ethyl acetate there is obtained pure 7-chloro-1-(2,3-dihydroxypropyl)-5-(2-fluorophenyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-one of melting point 117°-118°C.

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