Acetyl- -aminonaphthalene

With aromatic amines such as benzidine, 4-aminobiphenyl and 2-aminonaphthalene, which cause bladder cancer, epidemiological evidence suggests that those with the slow acetylator phenotype who have occupational exposure are more at risk. In contrast, with the heterocyclic amines produced in food by cooking, such as PhIP, which cause colon cancer, it seems from similar evidence that fast acetylators are more at risk. 

The use of pyridine during final coupling (pyridine coupling) is illustrated in the following abridged manufacturing specification for C. I. Direct Green 33, 34270 2-aminonaphthalene-8-sulfonic acid —> 3,5-xylidine- 2-ethoxy Cleve acid-6— A-acetyl H acid... 

Aromatic amines are often acetylated before nitration. Examples include the nitration of p-acetotoluide and 2-acety]aminonaphthalene, the products being 3-nitro-p-acetotoluide (90%) and l-nitro-2-acetylamino-naphthalene (49%), respectively. The p-tolylsulfonyl derivative is readily formed and hydrolyzed after nitration. On the other hand, if unacetylated and in the presence of a large excess of sulfuric acid, p-toluidine gives mainly 2-nitro-p-toluidine (71%), the arylammon um ion being meta-directing. 

This procedure is based upon previous studies of the nitration of 2-acetyl-/3-aminonaphthalene.i... 

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