ChemicalBook CAS DataBase List 3-CYANO-5-METHYLINDOLE

3-CYANO-5-METHYLINDOLE synthesis

6synthesis methods

Product Name:3-CYANO-5-METHYLINDOLE
CAS Number:194490-13-6
Molecular formula:C10H8N2
Molecular Weight:156.18

52562-50-2 Synthesis

52562-50-2
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194490-13-6
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Yield:194490-13-6 67%

Reaction Conditions:

with formic acid;hydroxylamine hydrochloride;sodium formate for 1 h;Heating / reflux;

Steps:

3.1

Example 3; 1. Synthesis of 3-cyanoindole derivatives with a terminal carboxylic acid; A basic synthetic method of a derivative with a terminal carboxylic acid is shown in the following scheme. [Show Image] An objective compound was prepared by (1) formylation of 3-position of the corresponding indole using phosphorus oxychloride in the presence of dimethylformamide (Vilsmeier method), (2) cyanation by dehydrating reaction with hydroxylamine in sodium formate and formic acid, (3) coupling with ethyl 4-fluorobenzoate in the presence of potassium fluoride on almina and 18-crown-5-ether in dimethylsulfoxide and then, (4) hydrolysis with lithium hydroxide in total 4 steps in that order. The results are shown in the following Table 1. In addition, XO-CH146 (R=H) was prepared from the third step using 3-cyanoindole purchased.; XO-CH158; XO-CH155 (0.600 g, 3.77 mmol) was dissolved in formic acid (6 mL), and to the solution were added hydroxylamine hydrochloride (0.31 g, 4.5 mmol) and sodium formate (0.47 g, 6.9 mmol), and the mixture was heated for reflux for an hour. To the reaction mixture was added water under ice-cooling, and the mixture was stirred for 1.5 hours. The solid was collected by filtration and dried 60°C under reduced pressure to give XO-CH158 as a purple solid (0.397 g, 67% yield).

References:

EP1932833,2008,A1 Location in patent:Page/Page column 11; 13

614-96-0 Synthesis