Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 13861-75-1, name is Spiro[cyclopropane-1,3′-indolin]-2′-one, A new synthetic method of this compound is introduced below., Formula: C10H9NO
A 5 mL microwave vial equipped with a stirrer bar was charged with spiro[cyclopropane-1,3?-indolin]-2?-one (20 mg, 0.125 mmol, 1 equiv) and MgI2 (1.74 mg, 6.25 mumol, 5 mol%) before being capped and purged with N2. THF (0.6 M, 0.2 mL) and trimethyl triazinane (18 muL, 0.125 mmol, 1 equiv) were then added and the reaction mixture was heated to 125 C in a sand-bath for 60 h. The reaction mixture was then cooled to r.t. before being diluted with EtOAc (5 mL) and washed with H2O (5 mL) and brine (5 mL). The organic layers were then passed through a hydrophobic frit and concentrated under vacuum before being purified (silica gel; EtOAc-petroleum ether, 50% then MeOH-CH2Cl2, 20%) to afford the desired product. Yield: 14 mg (55%); pale-yellow oil. IR (solid): 3192, 3060, 2943, 2787, 1707, 1619, 1472, 1336, 1195 cm-1. 1H NMR (400 MHz, CDCl3): delta = 8.45 (s, 1 H), 7.41 (d, J = 7.3 Hz, 1 H), 7.19 (td, J = 7.7, 1.2 Hz, 1 H), 7.04 (td, J = 7.6, 1.0 Hz, 1 H), 6.89 (d, J =7.7 Hz, 1 H), 3.11-3.00 (m, 1 H), 2.91 (s, 2 H), 2.88-2.74 (m, 1 H), 2.49 (s, 3 H), 2.41 (ddd, J = 12.5, 7.7, 4.7 Hz, 1 H), 2.12 (dt, J = 12.9, 7.5 Hz,1 H). 13C NMR (101 MHz, CDCl3): delta = 182.7, 140.1, 136.0, 127.8, 123.4, 122.9, 109.5, 66.2, 56.7, 53.6, 41.8, 38.0. HRMS (NSI): m/z [M + H]+ calcd for C12H15N2O: 203.1179; found: 203.1177.
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; Seath, Ciaran P.; Fyfe, James W. B.; Molloy, John J.; Watson, Allan J. B.; Synthesis; vol. 49; 4; (2017); p. 891 – 898;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem