Application of 3891-07-4,Some common heterocyclic compound, 3891-07-4, name is 2-(2-Hydroxyethyl)isoindoline-1,3-dione, molecular formula is C10H9NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Under nitrogen, to a cooled (0 C) solution of Ph3P (9.44 g, 36 mmol) in dry THF (60 mL), diisopropylazodicarboxylate (DIAD) (7.08 mL, 36 mmol) was added dropwise at stirring. The suspension obtained was stirred for 30 min and then a suspension of calixarene 9 (1:1 p-xylene complex, 6.40 g, 6 mmol) and 2-hydroxyethylpthalimide (6.88 g, 36 mmol) in THF (200 mL) was added dropwise. The stirring was continued for 1 h at low temperature and then for 24 h at room temperature. The reaction mixture (clear solution) was concentrated in vacuo to an oil, which was triturated with methanol. The solid formed was separated, washed with methanol and dried. Yield 89% (6.98 g, white powder). Mp 234-236 C (decomp.). 1H NMR (400 MHz, CDCl3) delta 7.93 (4H, m, ArHPht), 7.70 (4H, m, ArHPht), 6.96 (4H, s, ArH), 6.67 (4H, s, ArH), 6.65 (2H, s, OH), 4.44 (4H, t, J=6.6 Hz, NCH2), 4.24 (4H, t, J=6.6 Hz, OCH2), 4.18 (4H, d, J=2.9 Hz, ArCH2Ar), 3.25 (4H, d, J=12.9 Hz, ArCH2Ar), 2.10-1.35 (60H, m, HAd). 13C NMR (100 MHz, CDCl3) delta 168.10 (CO), 150.47, 149.01, 146.87, 141.49 (CAr), 133.83 (CHAr,Pht), 132.13, 132.09 (CAr), 127.72 (CAr,Pht), 124.96, 124.26 (CHAr), 123.22 (CHAr,Pht), 71.79 (OCH2), 43.70, 42.74 (CAd), 37.47 (NCH2), 36.91, 36.61 (CAd), 35.29, 35.26 (CAd), 31.11 (ArCH2Ar), 29.08, 28.76 (CHAd). FD-MS: m/z 1308.5 [M+H]+; C88H94N2O8·H (1308.7).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(2-Hydroxyethyl)isoindoline-1,3-dione, its application will become more common.
Reference:
Article; Vatsouro, Ivan; Serebryannikova, Alina; Wang, Leyong; Hubscher-Bruder, Veronique; Shokova, Elvira; Bolte, Michael; Arnaud-Neu, Franoise; Boehmer, Volker; Kovalev, Vladimir; Tetrahedron; vol. 67; 42; (2011); p. 8092 – 8101;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem