Preparation method of 3-(4-hydroxybutyl)-1H-indole compound
A technology of hydroxybutyl and indole, which is applied in the field of preparation of 3--1H-indole compounds, can solve problems such as inapplicability to industrial production and difficulties, and achieve short reaction time, short reaction route and high yield Effect
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[0024] The invention provides a kind of preparation method of 3-(4-hydroxybutyl)-1H-indole compound, comprises the following steps:
[0025] Dissolving 5-substituted indole compounds in tetrahydrofuran, reacting with anhydrous aluminum trichloride catalysis, and post-processing after the reaction to obtain 3-(4-hydroxybutyl)-1H-indole compounds;
[0026] The chemical structural formula of 5-substituted indole compounds is as shown in formula (I), and the chemical structural formula of 3-(4-hydroxybutyl)-1H-indole compounds is as shown in formula (II):
[0027]
[0028] Among them, R 1 is hydrogen, C1-C3 alkyl, cyano or C1-C3 alkoxy.
[0029] In one embodiment of the invention, R 1 For hydrogen, methoxy, methyl, cyano.
[0030] In one embodiment of the present invention, the volume ratio of 5-substituted indole compound to tetrahydrofuran is 1:10-15.
[0031] In one embodiment of the present invention, the molar ratio of the 5-substituted indole compound to the anhydrous...
Embodiment 1
[0041] This example provides a preparation method of 3-(4-hydroxybutyl)-1H-indole compound: 3-(4-hydroxybutyl)-1H-indole-5-cyanide.
[0042] The preparation of 3-(4-hydroxybutyl)-1H-indole-5-formyl cyanide, its reaction formula is as follows:
[0043]
[0044] Dissolve 5-cyanindole (14.2g, 0.1mol) in tetrahydrofuran (200mL), control the internal temperature below 50°C, add anhydrous aluminum trichloride (14.7g, 0.11mol) and mix well; heat up to The reaction temperature was 50°C, and the reaction was carried out for 4h. After the reaction, slowly pour the reaction solution into 1N 50mL dilute hydrochloric acid (quenched), stir for 10min, separate the liquids, and then extract the aqueous phase with 100mL tetrahydrofuran; combine the organic phases, wash with 50mL saturated saline, and dry over anhydrous sodium sulfate Concentration gave a yellow oil, and 18.2 g of a white solid was obtained by column chromatography, with a yield of 82%.
[0045] ESI-MS[M+H] + : 215.12
...
Embodiment 2-4
[0048] The method of Example 1 was used to prepare 3-(4-hydroxybutyl)-1H-indole compounds, and the reaction conditions and results are shown in Table 1.
[0049] Table 1 embodiment 2-4 reaction conditions and result summary
[0050]
[0051]
[0052] The results in Table 1 show that the method of the present invention can obtain the target product in high yield.
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