N-[Hydroxy(amino)alkyl]amides of amino(nitro)benzoic acids

2-Aminoethanol and 3-amino-1-propanol react with methyl 3-nitro- and 4-nitr obenzoates in boiling toluene to afford the corresponding ethyl N-(hydroxya lkyl)nitrobenzoates. The reaction of methyl 3-nitro- and 4-nitrobenzoates w ith bis(2-hydroxyethyl)amine yields bis(2-hydroxyethyl)ammonium 3-nitro- an d 4-nitrobenzoates. Bis(2-aminoethyl)amine reacts with nitrobenzoic acid es ters regioselectively at the primary amino group. The nitro group in N-[hyd roxy(amino)alkyl]nitrobenzamides is readily reduced to amino with hydrazine hydrate in the presence of iron(III) chloride and charcoal in boiling etha nol.