Methylamine → N-methyl-3-nitrobenzamide

HRID 1270553Notes

Reaction equation

HRID 1270553 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](O)=[O:8])([O-:3])=[O:2].[CH3:13][NH2:14]>C(Cl)CCl>[CH3:13][NH:14][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 84973-Nitrobenzoic acid

Product 1

HCID 221964N-methyl-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Commercially available 3-nitrobenzoic acid is reacted with methylamine and EDC under standard conditions to afford N-methyl-3-nitrobenzamide, which is reduced with LAH under standard conditions to afford N-methyl(3-nitrophenyl)methanamine, which is protected with benzylchloroformate under standard conditions to yield t-butyl 3-nitrobenzylmethylcarbamate. This material is nitrosated and reduced to yield t-butyl 3-hydrzazinobenzylmethylcarbamate.

Sources & evidence

ORD record
ord-8cb17a89dedb4ed89a1ee1d5cfd4bacb
Source dataset
uspto-grants-2007_04
Patent number
US07202257B2

Reaction notes

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