77317-55-6, A common compound: 77317-55-6, name is Methyl 2-amino-5-iodobenzoate, belongs to iodides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
To a stirred solution of methyl 6-iodoanthranilate (53) (4.46 g, 16.1 mmol) in ethyl orthoformate (8.92 mL, 53.5 mmol) was added 2,2-dimethyl-1,3-dioxane-4,6-dione (1.16 g, 8.05 mmol). The mixture was stirred at 80 C for 45 min. After cooling to room temperature, the yellow precipitate was filtered and washed with ethanol (2 x 10 mL) to give methyl 2-[(2,2-dimethyl-4,6-dioxo[1,3]dioxan-5-ylidenemethyl)amino]-5-iodobenzoate (54) (3.31 g, 7.68 mmol) as a yellow solid. Yield 95%; mp 206-208 C; IR (KBr) nu 1198, 1227, 1251, 1284, 1429, 1585, 1607, 1685, 3100-3250 cm-1; 1HNMR (200 MHz, CDCl3) delta 1.07 (s, 6H, (CH3)2C), 3.98 (s, 3H, CH3O), 7.23 (d, 1H, J = 8.8 Hz), 7.86 (dd, 1H, J = 2.0, 8.8 Hz, H-3), 8.38 (d, 1H, J = 2.0 Hz, H-4), 8.65 (d, 1H, J = 14.0 Hz, C=CH-NH), 13.1 (d, 1H, J = 14.0 Hz, NH); 13C NMR (50 MHz, CDCl3) delta 27.2 ((CH3)2C), 53.2 (CH3O), 88.5 (C-5), 89.9 (C=CH-NH), 105.1 ((CH3)2C), 117.6 (C-3), 119.7 (C-1), 139.5 (C-2), 140.8 (C-6), 143.2 (C-4), 150.4 (C=CH-NH) 163.6 (CO), 164.0 (CO), 165.3 (CO); ESI-MS m/z 373.89 [M-CH3O-CO + H]+.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Methyl 2-amino-5-iodobenzoate, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Billaud, Emilie M.F.; Maisonial-Besset, Aurelie; Rbah-Vidal, Latifa; Vidal, Aurelien; Besse, Sophie; Bequignat, Jean-Baptiste; Decombat, Caroline; Degoul, Francoise; Audin, Laurent; Deloye, Jean-Bernard; Dolle, Frederic; Kuhnast, Bertrand; Madelmont, Jean-Claude; Tarrit, Sebastien; Galmier, Marie-Josephe; Borel, Michele; Auzeloux, Philippe; Miot-Noirault, Elisabeth; Chezal, Jean-Michel; European Journal of Medicinal Chemistry; vol. 92; (2015); p. 818 – 838;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com