Journal of Heterocyclic Chemistry p. 257 - 262,258,261 (1979)
Update date:2022-08-10
Topics:
Patton
Dudley
The synthesis of 2-methyl-5H-dibenz[b,f]azepine-5-carboxamide (2-methylcarbamazepine, 2-MCBZ), a promising internal standard for chromatographic assays of the antiepileptic agent carbamazepine is described. N-(p-tolyl)anthranilic acid was utilized as a starting material for the synthesis of a key compound, 2,9-dimethylacridine, which was converted in two steps to 2-methyl-9-hydroxymethylacridan. The acridan, in the presence of polyphosphoric acid, was ring-expanded to form 2-methyl-5H-dibenz[b,f]azepine, this latter compound being converted by conventional reactions to its 5-carbamyl derivative, 2-MCBZ.
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