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2-(2-(2-hydroxyethoxy)ethyl)isoindoline-1,3-dione synthesis

7synthesis methods
-

Yield: 99%

Reaction Conditions:

in toluene for 6 h;Reflux;Dean-Stark;

Steps:

2-(2-(2-hydroxyethoxy)ethyl)isoindoline-1 ,3-dione (128).
2-(2-aminoethyl)-ethanol (2.10 g, 19.94 mmol) and phthalic anhydride (2.95 g, 19.94 mmol) were dissolved in 90 mL toluene and the resulting solution was then heated under reflux for 6 h with Dean-Stark apparatus. The reaction mixture was allowed to cool, dried over MgSO4, filtered, and concentrated under diminished pressure afforded compound 128 as a white solid: yield 4.67 g (99%); silica gel TLC Rf 0.35 (1:2 hexanes-ethyl acetate); ‘H NMR (CDC13) ö 3.61 (m, 2H), 3.69 (m, 2H), 3.75 (t, 2H, J = 5.3Hz), 3.91 (t, 2H, J = 5.3Hz), 7.73 (m, 2H), 7.85 (m, 2H, m).

References:

ARIZONA BOARD OF REGENTS, for and on behalf of ARIZONA STATE UNIVERSITY;HECHT, Sidney;MADATHIL, Manikandadas;BHATTACHARYA, Chandrabali;BOZEMAN, Trevor;PAUL, Rakesh;YU, Zhiqiang;RISHEL, Michael, J. WO2014/152718, 2014, A1 Location in patent:Paragraph 0342