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Directed lithiation of 3,5-dichloroaniline and its application in the synthesis of 1,3-dichloro-6,7,8,9,10,12-hexahydroazepino[2,1-b][5-14C]quinazoline monohydrochloride

✍ Scribed by I. Victor Ekhato; Che C. Huang

Publisher
John Wiley and Sons
Year
1994
Tongue
French
Weight
421 KB
Volume
34
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

1,3‐Dichloro‐6,7,8,9,10,12‐hexahydroazepino[2,1‐b][5‐^14^C]quinazoline monohydrochloride (1) was synthesized in 12% overall yield starting from 3,5‐dichloroaniline, and a radiochemical purity of 99.6% was obtained. The synthetic sequence was facilitated by the regio‐controlled preparation of 4,6‐dichloroanthranilic acid (3) from 3,5‐dichloroaniline using the t‐butoxycarbonyl‐protected aniline and t‐butyllithium/tetramethylethylenediamine (t‐BuLi/TMEDA) combination followed by carboxylation. The quinazoline monochloride 1 was constructed by condensation of 3 with 1‐aza‐2‐methoxyl‐cycloheptene and then reduction.

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