2-Nitrotoluene → N-(2-Methylphenyl)hydroxylamine

Participants

Reaction Steps

The 2-N(OZ)CO2CH3 -benzylbromide, methyl N-(2-bromomethylphenyl)-N-alkoxycarbamate, is prepared as described in both EP619301 and EP704430 in a 4 step sequence as shown in scheme B. As described in the aforementioned European patent applications o-nitrotoluene is reacted with ammonium chloride in the presence of zinc to provide N-2-methyl phenyl hydroxylamine (XI) as described in Organic Synthesis Collective Volume III, p.668. The hydroxylamine is acylated with methyl chloroformate to provide the methyl phenyl N-hydroxycarbamate (XII) which is alkylated, for example with dimethylsulfate (R is methyl), to provide (XIII) which is brominated under standard conditions such as N-bromosuccinimide in carbon tetrachloride in the presence of a catalyst such as benzoyl peroxide to afford the intermediate benzylbromide (XIV). ##STR9##

Provenance & Evidence