Methylamine → N-methyl-3-nitrobenzamide

HRID 16991

Reaktionsgleichung

Reaktionsgleichung von HRID 16991
[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

Komponenten

4

Edukt 2

HCID 6329MethylamineHCID 84973-Nitrobenzoic acid

Produkt 1

HCID 221964N-methyl-3-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

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.

Quellen und Nachweise

ORD-Eintrag
ord-4942823dcd4342c18d70523434e585ba
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737283B2

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