10-Methoxyiminostilbene → 10-methoxy-5H-dibenz(b,f)azepine-5-carboxamide

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Reaction Steps

Acetic acid (150 mL) is added dropwise to a stirred mixture of 10-methoxy-5H-dibenzo[b,f]azepine (25.0 g, 112 mmol) and NaOCN (9.25 g, 142 mmol) under a nitrogen atmosphere at room temperature. After stirring for 7 hours the resulting yellow suspension of the title compound (>95% area of the compound by HPLC) is used for synthesis of 10-oxo-10,11-dihydro-dibenzo[b,f]azepine-S-carboxylic acid amide. The title compound can be isolated by adding 1N NaOH to a pH of ≧8 followed by extraction with toluene. Drying of the combined organic layers and concentration in vacuo yields the title compound as a light yellow solid (yield≧75%).

Provenance & Evidence