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. 19155-24-9, name is 3,3-Dimethylindolin-2-one, A new synthetic method of this compound is introduced below., COA of Formula: C10H11NO
To a mixture of 3,3-dimethyloxindole 41 (50 mg, 0.31mmol, 1.00 equiv) and Cs2CO3 (202 mg, 0.62 mmol, 2.00 equiv) in THF (1.60 mL)was added p-nitrobenzyl bromide (101 mg, 0.47 mmol, 1.50 equiv). The reactionmixture was stirred overnight. Then, the reaction mixture was extracted with EtOAc(3 x 3 mL) and washed with brine. The combined organic phases were dried overMgSO4 and concentrated in vacuo. The residue was purified by columnchromatography (1:4 ? 1:2 EtOAc:hexanes) on silica gel to afford N?4-nitrobenzyl-3,3-dimethyloxindole 3c (77.5 mg, 84percent yield).Rf = 0.35 (1:2 EtOAc:hexanes); 1H NMR (500 MHz, CDCl3) delta 8.18 (d, J = 8.8 Hz,2H), 7.43 (d, J = 10.0 Hz, 2H), 7.25 (ddd, J = 7.3, 1.5, 0.7 Hz, 1H), 7.16 (td, J = 7.7,1.3 Hz, 1H), 7.07 (td, J = 7.5, 1.1 Hz, 1H), 6.65 (dt, J = 7.7, 0.7 Hz, 1H), 5.01 (s, 2H),1.45 (s, 6H); 13C NMR (126 MHz, CDCl3) delta 181.6, 147.6, 143.7, 141.1, 135.8, 128.0,127.9, 124.2, 123.2, 122.8, 108.7, 77.2, 44.4, 43.1, 24.7; IR (Neat Film NaCl) 2968,1707, 1613, 1522, 1343, 1173, 1111, 1009, 760; HRMS (MM: ESI-APCI+) m/zcalc?d for C17H17N2O3 [M+H]+ : 297.1234; found: 297.1239.
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; Han, Seo-Jung; Fernando De Melo, Gabriel; Stoltz, Brian M.; Tetrahedron Letters; vol. 55; 47; (2014); p. 6467 – 6469;,
Indoline – Wikipedia,
Indoline | C8H9N – PubChem