Chinese Journal of Organic Chemistry >
Process Improvement on the Synthesis of Nitidine Chloride
Received date: 2014-12-20
Revised date: 2015-01-28
Online published: 2015-02-10
Supported by
Project supported by the NSFC (No. 81230090), the Shanghai Leading Academic Discipline Project (No. B906).
Nitidine chloride was synthesized via reductive amination, intramolecular Heck coupling reaction, aromatization, methlyation and ion exchange, using 6-bromine-3,4-dimethoxybenzaldehyde and 6,7-methylenedioy-1-naphthylamine as starting material. The key intramolecular Heck coupling reaction was optimized, and acetic acid palladium(II) [Pd(OAc)2], tris(2-methylphenyl)phosphine [P(o-tol)3] and N,N-dimethylformamide (DMF) system was confirmed as the most efficient conditions. The total yield was increased significantly, and the optimal conditions may also be applied to the synthesis of other benzo[c]phenanthridine alkaloid.
Key words： nitidine chloride; intramolecular Heck reaction; synthesis
Xu Xusheng , Liu Zhiqian , Shao Wenhao , Ye Ji , Sun Qingyan , He Weiwei , Zhang Weidong . Process Improvement on the Synthesis of Nitidine Chloride[J]. Chinese Journal of Organic Chemistry, 2015 , 35(6) : 1353 -1356 . DOI: 10.6023/cjoc201412036
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