103718-97-4Relevant articles and documents
Reinvestigation of a 5H-Dibenzotriazonine Synthesis
Peet, Norton P.,Sunder, Shyam,Barbuch, Robert J.,Whalon, Michael R.,Huber, Edward W.,Huffman, John C.
, p. 1611 - 1618 (2007/10/02)
Treatment of 5-chloro-2-aminobenzophenone (1) with o-phenylenediamine, sodium acetate, and acetic acid gave 2-(acetyl)amino-5-chlorobenzophenone (5) rather than N--1,2-benzenediamine (3), as reported by Kulkarni et al.Authentic 3 was prepared and treated with chloroacetic acid and polyphosphoric acid (PPA) to give 1, recovered 3, 2,8-dichloro-6,12-diphenyldibenzodiazocine (9) and 2-chloro-6-(chloromethyl)-13-phenyl-5H-dibenzotriazonine (10).Treatment of 5 with PPA, with or without chloroacetic acid, gave phenyl> phenylmethanone (11) as the sole product in 90percent yield.Treatment of other benzophenones, acetophenones, and anilines with sodium acetate and acetic acid provided acetanilides in 78-96percent yield, with the exception of 2'-aminoacetophenone (20), wich gave a quantitative yield of 2--4-methylquinoline (21).The mechanism of acetanilide formation with sodium acetate and acetic acid is discussed.The structure of 21 was established using high resolution 1H nmr techniques.Attempts to prepare an authentic sample of 21 from 2-chlorolepidine (26) and (20) gave 4-methyl-N--2-quinolinamine (29) as the major product.
