Synthetic Route of 6780-38-7, A common heterocyclic compound, 6780-38-7, name is 2-(1,3-Dioxoisoindolin-2-yl)acetyl chloride, molecular formula is C10H6ClNO3, its 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.
General procedure: To a stirred solution of 3 (10.00 g, 54.57 mmol) and triethylamine (15.21 mL, 109.10mmol) in 200 mL CHCl3 at 5-10 C a solution of phthalylglycyl chloride 4 (14.64 g, 65,48 mmol) in CHCl3 (50 mL) was added dropwise over 30 min. During the chlorideaddition the product precipitated. The mixture was stirred additionally at 24 oC for 30min and then chloroform (1.50 L) was added to completely dissolve the product. Theorganic phase was washed with water (300 mL), 5% sodium carbonate solution (300mL) and water (300 mL) and dried over MgSO4. The solution was concentrated invacuo to 1/3 of the initial volume and after cooling to 10 C the precipitated productwas filtered off to give 17.60 g (87%) of product 5 as pale beige solid; mp = 234-235C. IR (KBr): 3269, 3063, 3026, 1772, 1732, 1666, 1587, 1541, 1413, 1257, 1211,952, 715 cm-1; 1H NMR (500 MHz, CDCl3): delta 3.99 (s, 2 H), 4.30 (s, 2 H), 7.05-7.18(m, 7 H, Ar), 7.22-7.30 (m, 2H, Ar), 7.75-7.77 (m, 2 H, Ar), 7.85-7.87 (m, 2 H, Ar); 13C NMR (125 MHz, CDCl3): delta 38.3, 41.6, 123.8, 124.1, 125.8, 126.7, 127.7, 128.1,128.9, 128.9, 131.0, 131.4, 131.9, 134.3, 135.1, 138.7, 164.2, 167.6; HRMS (ESI):m/z calcd for C23H18N2O3Na [M+Na]+: 393.1215; found: 393.1223.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Article; Roszkowski, Piotr; Maurin; Czarnocki, Zbigniew; Beilstein Journal of Organic Chemistry; vol. 11; (2015); p. 1509 – 1513;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem