1) aniline -> benzamide
diazotize the aniline and trap out with CO2 to form benzonic acid, then make an amide. probably easiest way is to make the acid chloride with (COCI)2 and then treat with NH3.
2 2 2
This reaction is also known as Hoffmann bromamide reaction .In this conversion of primary amide to a primary amine containing one carbon atom less than the original amide on heating with mixture of Brâ‚‚ in presence of NaOH or KOH (i.e. NaOBr or KOBr) is called Hofmann bromamide reaction.
Please see the attachment in that I have shown the conversion .