1H-Benz[de]isoquinoline-1,3(2H)-dione,2-(2-hydroxyethyl)-6-(4-morpholinyl)- synthesis
- Product Name:1H-Benz[de]isoquinoline-1,3(2H)-dione,2-(2-hydroxyethyl)-6-(4-morpholinyl)-
- CAS Number:164584-67-2
- Molecular formula:C18H18N2O4
- Molecular Weight:326.35
![6-bromo-2-(2-hydroxyethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione](/CAS/20180711/GIF/52559-37-2.gif)
Yield:164584-67-2 60%
Reaction Conditions:
with tris(dibenzylideneacetone)dipalladium(0) chloroform complex;caesium carbonate;4,5-bis(diphenylphosphino)-9,9-dimethylxanthene in toluene at 60; for 48 h;Buchwald-Hartwig Coupling;Reagent/catalyst;Solvent;Temperature;
Steps:
12
General procedure: General procedure 2: Compound 12 (100 mg, 0.31 mmol), Pd2(dba)3·CHCl3 (10 mg, 0.01 mmol), Xantphos (6 mg, 0.01 mmol), morpholine (82 mg, 0.94 mmol) and Cs2CO3 (305 mg, 0.94 mmol) were heated at 60 °C for 48 h.
Purification by flash column chromatography (2% MeOH in 1:1 EtOAc/Pet Spirits) afforded the title compound (60 mg, 60%, Rf = 0.16) as a bright yellow solid; mp 166-168 °C; 1H NMR (270 MHz, CDCl3): δ 2.18 (br s, 1H), 3.28 (app. t, Japp. = 4.3 Hz, 4H), 3.97 (t, J = 5.2 Hz, 2H), 4.03 (app. t, Japp. = 4.6 Hz, 4H), 4.46 (t, J = 5.2 Hz, 2H), 7.24 (d, J = 2.9 Hz, 1H), 7.71 (t, J = 7.6 Hz, 1H), 8.44 (d, J = 8.6 Hz, 1H), 8.54 (d, J = 7.9 Hz, 1H), 8.60 (d, J = 7.2 Hz, 1H); 13C NMR (67.5 MHz, CDCl3): δ 42.9, 53.5, 62.2, 67.0, 115.1, 116.9, 123.1, 126.0, 126.2, 130.1, 130.5, 131.6, 133.0, 156.0, 165.0, 165.4; HRMS (ESI-TOF) m/z: [M + H]+ Calcd for C18H18N2O4 327.1339; Found 327.1354.
References:
Fleming, Cassandra L.;Ashton, Trent D.;Pfeffer, Frederick M. [Dyes and Pigments,2014,vol. 109,p. 135 - 143]
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![6-morpholinobenzo[de]isochromene-1,3-dione](/CAS/20180703/GIF/31837-36-2.gif)
