Electric Literature of 6780-38-7,Some common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, 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.
To a solution of tert-butyl 3-amino-4-methylphenylcarbamate (0.667 g, 3 mmol), 2-(l,3-dioxoisoindolin-2-yl)acetyl chloride (0.671 g, 3.00 mmol) in DCM (10 mL) was added diisopropylethylamine (1.048 mL, 6.00 mmol). After stirring 25 C for 15 h, saturated aqueous sodium chloride (25 mL) was added and extracted with ethyl acetate (3 x 25 mL). The organic layers were combined, dried (MgSO4), filtered, and concentrated. The crude product was purified by silica gel chromatography (100% ethyl acetate) to give the title compound as a white solid (1.15 g, 2.81 mmol, 94% yield); 1H NMR (400 MHz, DMSO-d6) delta 9.70 (s, IH), 9.29 (s, IH), 7.91 – 7.99 (m, 2H), 7.83 – 7.91 (m, 2H), 7.56 (s, IH), 7.13 (d, J= 8.20 Hz, IH), 7.07 (d, J- 8.20 Hz, IH), 4.45 (s, 2H), 2.11 (s, 3H), 1.45 (s, 9H).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, its application will become more common.
Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Indoline – Wikipedia,
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