Welcome to chemicalbook!
Chinese English Japanese Germany Korea
400-158-6606
Try our best to find the right business for you.
Do not miss inquiry messages Please log in to view all inquiry messages.

Welcome back!

2-[(4-NITROBENZYL)OXY]-1H-ISOINDOLE-1,3(2H)-DIONE synthesis

4synthesis methods
-

Yield:30777-85-6 97%

Reaction Conditions:

with N-ethyl-N,N-diisopropylamine in tetrahydrofuran; for 24 h;Heating / reflux;

Steps:

I

iV-(4-Nitrobenzyloxy)phthalimide (18); A magnetically stirred solution of 7V-hydroxyphthalimide (16) (11.2 g, 68.7 mmol) in THF (200 mL) was treated with 4-nitrobenzylbromide (17) (13.5 g, 62.5 mmol) and NJV- diisopropylethylamine (21.8 mL) and the resulting mixture heated at reflux for 24 h. The reaction mixture was then cooled and the solvent removed under reduced pressure. The ensuing residue was partitioned between H2O (150 mL) and CH2Cl2 (150 mL), the organic phase separated and the aqueous phase extracted with CH2Cl2 (1 x 100 mL). The combined organic fractions were dried (MgSO4), filtered and concentrated under reduced pressure and the resulting solid triturated with MeOH (150 mL). The ensuing solid was removed by filtration to afford the title compound 185 (18.1 g, 97%) as a cream solid, m.p. 194.1- 195.1 °C (lit.5 m.p. 197-198 0C).1H NMR (300 MHz) δ 8.24 (d, J 8.7 Hz, 2H), 7.84-7.22 (complex m, 6H), 5.31 (s, 2H).

References:

WO2008/124878,2008,A1 Location in patent:Page/Page column 41-42