Aminate it where? On the ring, or on the methyl group? Both answers are yes of course.
To aminate the ring: You could nitrate it with nitric acid and sulfuric acid, or a nitrate salt and sulfuric acid, followed by reduction of the nitro group(s) to form the amine(s). This gives a mixture of three possible isomers, but if a nitrate salt is used, you really only get two of them in apreciable amounts: the ortho and para isomers. You can further tweak isomer selectivity (somewhat) by using specific salts of nitric acid, namely sodium for para and potassium for ortho.
You can also use ammonia, toluene, and catalytic ammonium iodide, with photolytic amination via a benzyne intermediate. There is a post in the Novel Discourse that offers some information about this. The information was read in a patent.
To aminate the methyl group, Im sure there are a bazillion ways, most starting from better things than toluene, but here's a few:
1.KMnO4 oxidation to benzoic acid, followed by distillation from ammonia, resulting in benzamide. Dehydrate this with P2O5 to cyanobenzene, and reduce this with sodium borohydride to benzylamine.
2.Chlorinate toluene with calcium hypochlorite, forming benzyl chloride, and react with ammonia.
3.Chlorinate toluene with calcium hypochlorite, forming benzyl chloride, react with sodium cyanide, forming phenylacetonitrile, hydrolyze to phenylacetic acid with sulfuric acid, then distill from ammonia, resulting in formation of phenylacetamide, and react with calcium hypochlorite to rip the carbonyl off, resulting in benzylamine.
4.many other and better ways, starting from things better than toluene.
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