3-Methyl-4-nitrobenzoic acid → alpha-[p-(dimethylamino)styryl]-N-(2-methyl-4-carboxyphenyl)nitrone

HRID 1033148Notes

Reaction equation

HRID 1033148 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[N+:11]([O-:13])=O)[C:5]([OH:7])=[O:6].[CH3:14][N:15]([CH3:26])[C:16]1[CH:25]=[CH:24][C:19]([CH:20]=[CH:21][CH:22]=O)=[CH:18][CH:17]=1>>[CH3:26][N:15]([CH3:14])[C:16]1[CH:25]=[CH:24][C:19]([CH:20]=[CH:21][CH:22]=[N+:11]([C:10]2[CH:9]=[CH:8][C:4]([C:5]([OH:7])=[O:6])=[CH:3][C:2]=2[CH3:1])[O-:13])=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 183703-Methyl-4-nitrobenzoic acidHCID 922244-(Dimethylamino)-cinnamaldehyde

Product 1

HCID 86747822alpha-[p-(dimethylamino)styryl]-N-(2-methyl-4-carboxyphenyl)nitroneYield 97.4%

Procedure

The general procedure of Example 1 was repeated except that 132.4 g (731 mmols) of 3 -methyl-4-nitrobenzoic acid was used instead of p-nitrobenzoic acid and 118.6 g (677 mmols) of 4-dimethylaminocinnamaldehyde was used instead of 4-diethylaminobenzaldehyde, thereby obtaining 213.8 g (yield 97.4%) of α-[p-(dimethylamino)styryl]-N-(2-methyl-4-carboxyphenyl)nitrone with a purity of 96%. The results of the analyses of the thus obtained compound are shown below.

Sources & evidence

ORD record
ord-f3fd399b812d4de2b4add459eb2b5145
Source dataset
uspto-grants-1994_05
Patent number
US05310620

Reaction notes

Loading…