2-Nitrotoluene → N-Hydroxy-2-toluidine
Reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH3:10])([O-])=[O:2].[Cl-].[NH4+]>[Zn]>[CH3:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[NH:1][OH:2]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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##
Sources & evidence
- ORD record
- ord-62da4d9f8f924f6ab596f2cf33b9138d
- Source dataset
- uspto-grants-2000_09
- Patent number
- US06114375
Reaction notes
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