Water → 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 200 ml of pyridine. 16 g of potassium permanganate in 300 ml of water are added dropwise within 20 minutes at room temperature to the well-stirred solution. After the potassium permanganate addition, the mixture is extensively concentrated on a rotary evaporator. The residue is briefly boiled out with ethyl acetate and filtered off under vacuum. The ethyl acetate filtrate is extracted with water, dried over magnesium sulfate, filtered and concentrated. The residue is dissolved in a small amount of ethyl acetate and seeded. By recrystallization of the first crystals 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.

Provenance & Evidence