Sodium Bisulfate → 10,11-Dihydro-10-oxo-5H-dibenz(b,f)azepine-5-carbonitrile

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Reaction Conditions

Reaction Steps

20 g (85 mmols) of (I) are dissolved in 120 ml of CH2Cl2. The solution is cooled to 0° C. and added with 0.24 g of 2,2,6,6-tetramethylpiperidine nitroxide, then with 180 ml of 1.4M NaClO, adjusted to pH 8.3 with a NaHSO4 saturated solution. The mixture is left for 1 hour at 0° C., then warmed to 20° C. for 4 hours. The organic phase is separated and washed with 50 ml of water, dried with 2 g of Na2SO4 and solvent is evaporated off. The residue is taken up with 50 ml of acetone and kept at 0° C. for 2 hours. The mixture is filtered, washed with 50 ml of cold acetone, dried at 60° C. for 4 hours to obtain 17 g of 5-cyano-10-oxo-10,11-dihydro-5H-dibenz[b,f]azepine (VII), m.p. 153-4° C., with 98.5% purity by HPLC (85% yield).

Provenance & Evidence