3-Nitrobenzamide → 3-Nitrobenzylamine

HRID 1392344Notes

Reaction equation

HRID 1392344 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

3

Reactant 2

HCID 125763-NitrobenzamideHCID 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 4-methoxybenzylisocyanate to afford 1-(3-nitrobenzyl)-3-(4-methoxybenzyl)urea. This material is subsequently reacted with oxalyl chloride to afford 1-(3-nitrybenzyl)-3-(4-methoxybenzyl)imidazolidine-2,4,5-trione whose nitro group is reduced and oxidized to afford 1-(3-hydrazinylbenzyl)-3-(4-methoxybenzyl)imidazolidine-2,4,5-trione. This material is deprotected with TFA under standard conditions to afford the title compound 1-(3-hydrazinylbenzyl)imidazolidine-2,4,5-trione.

Sources & evidence

ORD record
ord-88aa6c1f8caa4f49b345f880e6f0bc60
Source dataset
uspto-grants-2008_03
Patent number
US07342037B2

Reaction notes

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