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. 672293-33-3, name is Methyl 4-amino-5-iodo-2-methylbenzoate, A new synthetic method of this compound is introduced below., Quality Control of Methyl 4-amino-5-iodo-2-methylbenzoate
To a solution of methyl 4-amino-5-iodo-2-methylbenzoate 2 (0.84 g, 2.90 mmol, 1 eq.) in DMF (10 mL), 2-oxobutyric acid (1.48 g, 14.5 mmol, 5 eq.) and DABCO (0.975 g, 8.7 mmol, 3 eq.) were added. The solution was stirred for 5 min and then palladium (II) diacetate (0.03 g, 0.145 mmol, 0.05 eq.) was added. The mixture was warmed to 105C, stirred during 16 h and then concentrated. The resulting solid was dissolved in AcOEt (150 mL) and washed with water (150 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated in vacuuo to obtain dark brown solid which was purified by trituration in AcOEt to give the desired indole 6 as grey powder (358 mg, 1.45 mmol, 50%); Mp : 280-282C (Dec.); Rf = 0.61 (SiO2, Cyc/AcOEt, 5/5); 1H NMR (400 MHz, CD3OD) 8.30 (s, 1H, H-4), 7.25 (s, 1H, H-7), 3.99 (s, 3H, CH3), 2.65 (s, 3H, CH3), 2.59 (s, 3H, CH3); 13C NMR (100 MHz, CD3OD) 168.1 (C=O), 165.3 (C=O), 139.6 (C), 137.2 (C), 128.0 (C), 127.7 (C), 125.6 (CH), 122.3 (C), 118.9 (C), 114.8 (CH), 52.1 (CH3), 22.9 (CH3), 9.94 (CH3); HR-ESIMS: [M-H]- m/z calcd for C13H12NO4 246.0766 found 246.0777.
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; Vogrig, Alexandre; Boucherle, Benjamin; Deokar, Hemantkumar; Thomas, Isabelle; Ripoche, Isabelle; Lian, Lu-Yun; Ducki, Sylvie; Bioorganic and Medicinal Chemistry Letters; vol. 21; 11; (2011); p. 3349 – 3353;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com