THE PREPARATION OF o- AND p-ACETAMINOBENZALDEHYDES

Abstract

Treatment of N,N-diacetyl-o-toluidine with N-bromosuccinilllide followed by hydrolysis of the intermediate dibromo compound gave o-acetanlinobenzaldehyde. The reaction was applied successfully to N,N-diacetyl-p-toluidine, N,Ndiacetyl-4-chloro-o-toluidine, 2,4-bis(diacetamino)toluene, and 4-acetosy-N,Ndiacetyl-o-toluidine.Both o-and p-acetaminobenzaldehyde were required for synthetic work in this laboratory. These compoullds have been prepared in the usual way b y the acetylation (6, 7) of o-and p-aminobenzaldehyde. However, the methods described in the literature for the preparation of o-aminobenzaldehyde by the reduction of o-nitrobenzaldehyde with ferrous sulplzate and ammonia (15) and for p-aminobenzaldehyde by the action of sodium polysulphide upon p-nitrotoluene (3) are tedious, and the products must be used immediately in order t o avoid self-condensation.A direct preparation of o-and p-acetaminobenzaldehyde was suggested b y the hydrolysis of N,N-diacetyl-p-toluidine (16) using aqueous sodium carbon-I ate which gave a quantitative yield of p-acetotoluidide, and also by the work of Brown and Newbold (2) who used N-bromosuccinimide to oxidize 4-

Design and Synthesis of Small Molecule Glycerol 3-Phosphate Acyltransferase Inhibitors

“…34 Free-radical bromination with NBS in CH 3 CN afforded benzyl bromide 9 , which was converted to phosphonate 10 through Arbuzov reaction with triethyl phosphite. The aniline was unmasked by exposure to a refluxing acidic solution of EtOH.…”

Scattered and diverse

“…The 'elsewhere', not surprisingly the title of one of the more recent collections by an Irish poet, 35 provides poets with an opportunity to look at the home in a critical, comparative manner, which often results in what John Brown aptly called 'mobile poems', 'bifocal visions'. 36 Apart from the familiar dislocations, to America (Muldoon) or England (Tom Paulin), there is a conspicuously growing number of 39 Affected by the rapid economic and social changes in the Ireland of the Celtic Tiger boom and in the political order in the North following the Good Friday Agreement, with no single group or coherent movement that would dominate the scene and inform its identity, it is a nomadic art of many voices, equally prone to probe into local traditions as to take on the risks of unstitching the patterns and looking for inspiration elsewhere, in 'further languages', in 'Zanzibar, Bombay, the Land of the Ethiops'.…”

Isoquinoline in the synthesis of 1-dichloromethylisoquinoline and 1-formylisoquinoline

“…Taking into account this information we tried further to convert compound I into aldehyde II, but the known methods of hydrolysis of the dichloromethyl group into the aldehyde one (acid [6], alkaline hydrolysis [7], and hydrolysis through morpholine derivatives [8]) were inefficient with compound I.…”