3-Nitrobenzamide → 3-Nitrobenzylamine

HRID 16993Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH2:9])=O)([O-:3])=[O:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:7][NH2:9])[CH:10]=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

Reactant 2

HCID 125763-Nitrobenzamide

HCID 21226445Aluminium lithium hydride

Product 1

HCID 1227223-Nitrobenzylamine

Procedure

Commercially available 3-nitrobenzamide is reduced with LAH under standard conditions to afford (3-nitrophenyl)methanamine, which is reacted with N-4-methoxybenzylsulfamic acid and EDC to afford 1-(4-methoxybenzyl)-3-benzylsulfonylurea. This material is reacted with oxalyl chloride to afford 1-(3-nitrobenzyl)-3-(4-methoxybenzyl)imidazolidine-2,2-dioxo-2-thio-4,5-trione whose nitro group is reduced and oxidized to afford 1-(3-hydrazinylbenzyl)-3-(4-methoxybenzyl)imidazolidine-2,2-dioxo-2-thio-4,5-trione. This material is deprotected with TFA under standard conditions to afford the title compound I-(3-hydrazinylbenzyl)imidazolidine-2,2-dioxo-2-thio-4,5-trione.

Sources & evidence

ORD record: ord-85310926569f41149255bdebe2e43fb0
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737283B2

Reaction notes

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