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

HRID 1023694Notes

Reaction equation

HRID 1023694 reaction equation
CO[C:3](=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10]Br.[CH2:13]([O:15][C:16](=[O:27])[CH2:17][CH2:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([NH2:26])=[CH:22][CH:21]=1)[CH3:14].NC1C=CC=CC=1>>[CH2:13]([O:15][C:16](=[O:27])[CH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([N:26]2[CH2:10][C:5]3[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=3)[C:3]2=[O:12])=[CH:24][CH:25]=1)[CH3:14]

Participants

4

Reactant 3

HCID 6115AnilineHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 10013251Ethyl 4-(4-aminophenyl)butanoate

Product 1

HCID 670449524-[4-(1-Oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester

Procedure

By using 2-bromomethyl-benzoic acid methyl ester and 4-(4-amino-phenyl)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-(1-oxo-1,3-dihydro-isoindol-2-yl)-phenyl]-butyric acid ethyl ester (Compound 19) as a white powdery substance.

Workup

  1. customused in Example 25, synthesis

Sources & evidence

ORD record
ord-58c96ef19b8e49dda857e04fe198f16a
Source dataset
uspto-grants-2014_05
Patent number
US08722723B2

Reaction notes

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