CH3NO2 (nitromethane) + Sn roofing nails + short chain alcohol (CH3OH, CH3CH2OH, CH3CH(OH)CH3, etc.) + HCl --> methylamine.hcl [CH3NH3+Cl-, a chloride salt]
CH3CH2OH (ethyl alcohol, the kind people drink) + PCl6 --> CH3CH2-Cl [ethyl chloride]
CH3CH2-Cl + HNO2 (nitrous acid, or HONO, which *does* have a nucleophilic lone pair of electrons intact on its central N atom) --> CH3CH2-NO2 [nitroethane]- HCl.