Formation of o-nitrosobenzaldehyde from hydrolysis of o-nitrobenzyl tosylate. Evidence of intramolecular nucleophilic interaction

Article abstract of DOI:10.1016/S0040-4039(98)01068-5

Hydrolysis of o-nitrobenzyl tosylate in CH₃CN:H₂O (1:1, v/v) gave o- nitrobenzyl alcohol and o-nitrosobenzaldehyde in 1.8 : 1 ratio. Formation of o-nitrosobenzaldehyde indicates that the nitro group participates in the leaving of the tosylate group. o-Nitrosobenzaldehyde was reduced by biological thiols to give o-aminobenzaldehyde. Reaction of o- nitrosobenzaldehyde with 1 tool of benzylamine afforded 3-(N- benzylamino)anthranil (or its tautomer) as a major product.