Reference of 77317-55-6, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 77317-55-6, name is Methyl 2-amino-5-iodobenzoate belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
A mixture of CuI (110 mg, 0.58 mmol), Pd(OAc)2 (60 mg, 0.27 mmol), and Ph3P (130 mg, 0.49 mmol) in MeCN (30 mL) deaerated (UST) under argon atmosphere was stirred at 20 C for 20 min. Iodide 6 (1.39 g, 5.0 mmol), Et3N (1.53 g, 15.11 mmol, 2.1 mL), H2O (0.15 g, 8.33 mmol), and finely ground CaC2 (1.0 g, 15.60 mmol) were then added. The reaction mixture was stirred for 7 h and concentrated in vacuo; the residue was extracted with hot EtOAc. The extract was filtered and concentrated in vacuo, the residue was purified by chromatography on SiO2 using gradient elution of PhH -> PhH/EtOAc (4 : 1). Diarylalkyne 2a (0.57 g, 70%) was isolated as yellow crystals, m.p. 245-249 C. HRMS (ESI), found m/z: 325.1179, 347.0997; C18H16N2O4; calculated 325.1183 [M + H]+, 347.1002 [M + Na]+. IR (KBr), nu/cm-1:788, 834, 985, 1103, 1162, 1235, 1300, 1430, 1506-1663, 1688, 2342, 2361, 2838-3033, 3367, 3464. 1H NMR (DMSO-d6), delta: 3.82 (s, 6 H, 2 MeO); 6.75 (d, 2 H, HC(5), HC(5), J = 8.6 Hz); 7.26 (dd, 2 H, HC(4), HC(4), J = 8.6 Hz, J = 1.9 Hz); 7.83 (d, 2 H, HC(2), HC(2), J = 1.9 Hz). 13C NMR (DMSO-d6), delta: 51.3 (Me, Me); 86.9 (CC); 108,8 (C(5), C(5)); 109.0 (C(3), C(3)); 116.9 (C(1), C(1)); 133.9 (C(2), C(2)); 136.0 (C(4), C(4)); 150.8 (C(6), C(6)); 167.1 (CO, CO).
The synthetic route of Methyl 2-amino-5-iodobenzoate has been constantly updated, and we look forward to future research findings.
Reference:
Article; Lozanova; Stepanov; Mel?nik; Zlokazov; Veselovsky; Russian Chemical Bulletin; vol. 68; 1; (2019); p. 64 – 67; Izv. Akad. Nauk, Ser. Khim.; 1; (2019); p. 64 – 67,4;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com