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Synthesis of 2‐methylcarbamazepine, a new internal standard for chromatographic assays of carbamazepine (tegretol ® )
Author(s) -
Patton Jeffrey R.,
Dudley Kenneth H.
Publication year - 1979
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570160213
Subject(s) - chemistry , azepine , anthranilic acid , carbamazepine , derivative (finance) , ring (chemistry) , chromatography , stereochemistry , medicinal chemistry , organic chemistry , epilepsy , neuroscience , financial economics , economics , biology
The synthesis of 2‐methyl‐5 H ‐dibenz[ b,f ]azepine‐5‐carboxamide (2‐methylcarbamazepine, 2‐MCBZ, 8), a promising internal standard for chromatographic assays of the antiepileptic agent carbamazepine (CBZ, 1), is described. N ‐( p ‐Tolyl)anthranilic acid (2) was utilized as a starting material for the synthesis of a key compound, 2,9‐dimethylacridine (4), which was converted in two steps to 2‐methyl‐9‐hydroxymethylacridan (6). The acridan 6, in the presence of poly‐phosphoric acid, was ring‐expanded to form 2‐methyl‐5 H ‐dibenz[ b,f ]azepine (7), this latter compound being converted by conventional reactions to its 5‐carbamyl derivative, 2‐MCBZ (8).