Aniline → 4-[4-(5-Nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester

HRID 1023691Notes

Reaction equation

HRID 1023691 reaction equation
CO[C:3](=[O:15])[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH2:13]Br.[CH2:16]([O:18][C:19](=[O:30])[CH2:20][CH2:21][CH2:22][C:23]1[CH:28]=[CH:27][C:26]([NH2:29])=[CH:25][CH:24]=1)[CH3:17].NC1C=CC=CC=1>>[CH2:16]([O:18][C:19](=[O:30])[CH2:20][CH2:21][CH2:22][C:23]1[CH:24]=[CH:25][C:26]([N:29]2[CH2:13][C:5]3[C:4](=[CH:9][CH:8]=[C:7]([N+:10]([O-:12])=[O:11])[CH:6]=3)[C:3]2=[O:15])=[CH:27][CH:28]=1)[CH3:17]

Participants

4

Reactant 3

HCID 6115AnilineHCID 10013251Ethyl 4-(4-aminophenyl)butanoateHCID 15088701Methyl 2-(bromomethyl)-4-nitrobenzoate

Product 1

HCID 670451994-[4-(5-Nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester

Procedure

By using 2-bromomethyl-4-nitrobenzoic acid methyl ester and 4-(4-aminophenyl)butyric acid ethyl ester instead of 2-bromomethyl-6-nitro-benzoic acid methyl ester and aniline used in Example 25, synthesis was performed in the same manner as that of Example 25 to obtain 4-[4-(5-nitro-1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester.

Workup

  1. customused in Example 25, synthesis

Sources & evidence

ORD record
ord-b4fabeccaaaa41c5a30e01b62a9eaa57
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Reaction notes

Loading…