Category: 354574-31-5

Application of 354574-31-5, 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. 354574-31-5, name is 2-Iodo-6-methoxyaniline belongs to iodides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A mixture of 2-iodo-6-methoxybenzenamine 10 (2.49 g, 10 mmol), methyl5-formylpentanoate 11 (1.59 g, 11 mmol) and DABCO (6.60 g, 30 mmol) in dry DMF (45 mL) was degassed for 20 min. Pd(OAc)2 (230 mg, 1 mmol) was added to the reaction,and the resulting mixture was heated at 85C under argon atmosphere overnight. The reaction mixture was cooled to room temperature and diluted with water followed by extraction with EtOAc.The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentratedin vacuo. The residue was purified by FCC (PE-Acetone, 8:1) to give 12 (1.43 g, 58%) as white foam.

The synthetic route of 2-Iodo-6-methoxyaniline has been constantly updated, and we look forward to future research findings.

Reference:
Article; Wang, Bin; Qin, Hua; Zhang, Fengying; Jia, Yanxing; Tetrahedron Letters; vol. 55; 9; (2014); p. 1561 – 1563;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com

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. 354574-31-5, name is 2-Iodo-6-methoxyaniline, A new synthetic method of this compound is introduced below., Formula: C7H8INO

EXAMPLE 2 Total Synthesis of Azagalanthamine 2.1 2-(1,4-dioxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxyphenyl)acetamide (16); A solution of (1,4-dioxaspiro[4.5]dec-7-en-8-yl) acetic acid (567 mg; 2.86 mmol; 1 eq) (7) and 2-iodo-6-methoxyaniline (1 g; 2.86 mmol; 1 eq) in anhydrous dichloromethane (30 mL) is admixed with 2-chloro-1-methylpyridinium iodide (1.46 g; 5.73 mmol; 2 eq) and triethylamine (3.98 mL; 28.65 mmol; 10 eq). The reaction mixture is heated at reflux for 20 hours. After cooling and acidification with iN HCl solution to pH=5-6, the mixture is extracted with dichloro-methane. The organic phases are washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and evaporated under vacuum. Purification by flash chromatography on silica gel (eluent: heptane/ethyl acetate 4/6) gives 1.10 g of 2-(1,4-di-oxaspiro[4.5]dec-7-en-8-yl)-N-(2′-iodo-6′-methoxy-phenyl)acetamide (16) in the form of a yellow foam (yield: 90%). Elemental analysis calculated for C17H20INO4 (m.p.: 429.25) C, 47.57; H, 4.70; N, 3.26; O, 14.91; found C, 47.39; H, 4.59; N, 3.01; O, 15.16. IR (CHCl3) nu (cm-1): 3382 (N-H); 1687 (CO) MS (ES) m/z: 429.8 [M+H]+. 1H NMR (CDCl3; 300 MHz) delta (ppm): 7.43 (dd, J=8.0, J=1.2; 1H; H3′); 7.18 (broad s; 1H; NH); 6.98 (t, J=8.0; 1H; H4′); 6.91 (dd, J=8.0, J=1.2; 1H; H5′); 5.72 (broad s; 1H; H4); 3.99 (s; 4H; Hdioxolane); 3.80 (s; 3H; OCH3); 3.15 (s; 2H; H2); 2.45 (broad s; 1H; H8); 2.37 (broad s; 1H; H5); 2.37 (broad s; 2H; H6); 1.85 (t, J=6.4; 2H; H7). 13C NMR (CDCl3; 62.9 MHz) delta (ppm): 169.2 (C(O)NH); 155.5 (C6′); 132.9 (Cl’); 130.8 (C3′); 129.6 (C4′); 128.1 (C8); 124.9 (C7); 111.7 (C5′); 107.7 (C5); 99.8 (C2′); 64.8 (Cdioxolane); 56.1 (OCH3); 45.7 (C2); 35.9 (C6); 38.2 (C4); 35.0 (C3).

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:
Patent; Thal, Claude; Guillou, Catherine; Beunard, Jean-Luc; Gras, Emmanuel; Potier, Pierre; US2005/65338; (2005); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com