2-Nitrobenzaldehyde → MS-1845

HRID 580080Notes

Reaction equation

HRID 580080 reaction equation
[N+:1]([CH:4](Br)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([O-])=O.[N+:12](C1C=CC=CC=1C=O)([O-:14])=[O:13].[C:23]1(=[O:33])N[C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]12.[K]>>[N+:12]([C:7]1[CH:6]=[C:5]([CH:10]=[CH:9][CH:8]=1)[CH2:4][N:1]1[C:26](=[O:28])[C:25]2=[CH:29][CH:30]=[CH:31][CH:32]=[C:24]2[C:23]1=[O:33])([O-:14])=[O:13]

Participants

4

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 11356361NitrobenzylbromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 309824MS-1845

Procedure

Nitrobenzylbromide is derived from nitrobenzaldehyde, which is then reacted with potassium phthalimide to obtain N-(m-nitrobenzyl)-phthalimide, and m-aminobenzylamine is produced with an yield of about 20% by a two-step reduction reaction (N. Kornblum et al, J. Am. Chem. Soc., 71, 2137 (1949)).

Sources & evidence

ORD record
ord-860aebe20ad1412ea9c59b5118ccfe00
Source dataset
uspto-grants-1988_06
Patent number
US04751328

Reaction notes

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