Phthalimide → N-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-3-pyridin-3-yl-acrylamide

HRID 458877Notes

Reaction equation

HRID 458877 reaction equation
O[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[CH:8]=[CH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.C(OC(N=NC(OCC)=O)=O)C>C1COCC1>[O:22]=[C:20]1[C:19]2[C:18](=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:17](=[O:27])[N:21]1[CH2:2][CH2:3][CH2:4][CH2:5][NH:6][C:7](=[O:16])[CH:8]=[CH:9][C:10]1[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6809PhthalimideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 53817888N-(4-hydroxybutyl)-3-pyridin-3-yl-acrylamide

Product 1

HCID 54145323N-[4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyl]-3-pyridin-3-yl-acrylamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Batch size: 7.8 g (35.4 mmol) N-(4-hydroxybutyl)-3-pyridin-3-yl-acrylamide, 9.3 g (35.4 mmol) tripdhenylphosphine, 5.2 g (35.4 μmmol) phthalimide and 6.2 g (35.4 mmol) azodicarboxylic acid diethyl ester in 100 ml THF.

Sources & evidence

ORD record
ord-abd07868b9d14f28bdbd3b7f409f121f
Source dataset
uspto-grants-2007_03
Patent number
US07192967B1

Reaction notes

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