4-Bromoacetanilide synthesis

Using a strategy of lactam synthesis with a combination of carbonylation and nitrogenation, 2-methyl- and 2-benzylquinazolin-4(3i/)-one 17 are obtained in 54 and 40% yield, respectively, on treatment of corresponding 2-bromoacetanilides 16 with tetrakis(triphenylphosphane)-palladium [Pd(Ph3P)J, potassium carbonate, and a titanium isocyanate complex in A-methyl-pyrrolidone under a carbon monoxide atmosphere. ... 

Synthesis of 62 from 60 is an example [51], Use of LiN(TMS)2 as the ammonia surrogate is problematic for aryl bromides containing an amide group, but the reaction of p-bromoacetanilide (63) proceeds smoothly using 2.2 equivalents of 61 [29],... 

Suppose, however, that we need o-nitroaniline. The synthesis that we just outlined would obviously not be a satisfactory method, for only a trace of o-nitroacetanilide is obtained in the nitration reaction. (The acetamido group is purely a para director in many reactions. Bromination of acetanilide, for example, gives/>-bromoacetanilide almost exclusively.)... 

In 1994, a procedure for the synthesis of benzo[c]-2,7-naphthyridines from pyridine methylstannanes and ort/jo-bromoacetanilides was reported based on a palladium catalyst. " By using CuO as a promoter, good yields of the products were formed (Scheme 3.26a). In 2004, Banwell s group reported the synthesis of quinolines, 2-quinolones, phenanthridines, and 6(5H)-phe-nanthridinones via palladium-mediated Ullmann cross-coupling of... 

Scheme 8.42 Synthesis of 3-aryloxindoles from A/-methyl-o-bromoacetanilide and aryl chlorides, as...

This methodology was extended to 2-bromoacetanilides en route to the synthesis of benzisoxazolo[2,3-a]p3Tidinium... 

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