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A kind of synthetic method of 4-nitroindole

A technology for nitroindole and nitroindole crude product, applied in the field of chemical synthesis, can solve the problems of affecting economic benefit, low recrystallization and vacuum biochemical yield, low 4-nitroindole yield, etc. The overall yield, the effect of improving the economic benefit of synthesis, and improving the total yield

Active Publication Date: 2019-04-26
SUZHOU RYAN PHARMACHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The synthesis method N-(2-methyl-3-nitrophenyl) ethoxymethanimine and 4-nitroindole crude product yields are higher, but recrystallization and vacuum biochemical yields are lower, Directly cause the final 4-nitroindole yield to be low, have influenced economic benefit, this synthetic method is the closest prior art of the present invention, and its synthetic route is

Method used

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  • A kind of synthetic method of 4-nitroindole
  • A kind of synthetic method of 4-nitroindole
  • A kind of synthetic method of 4-nitroindole

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0040] A kind of synthetic method of 4-nitroindole, main process parameter is:

[0041] With 2-methyl-3-nitroaniline and triethyl orthoformate under the catalysis of benzoic acid, react to generate N-(2-methyl-3-nitrophenyl) ethoxymethimine, benzoic acid The added amount is 5% of the amount of 2-methyl-3 nitroaniline substance;

[0042] The molar mass ratio of 2-methyl-3-nitroaniline to triethyl orthoformate is 0.9:1;

[0043] N-(2-methyl-3-nitrophenyl) ethoxymethanimine reacts with sodium ethylate and diethyl oxalate to generate 4-nitroindole crude product;

[0044] The molar ratio of sodium ethylate and diethyl oxalate is n (sodium ethylate):n (diethyl oxalate)=1.1:1;

[0045] The molar ratio of 2-methyl-3-nitrophenyl) ethoxymethylimine to potassium ethoxide and diethyl oxalate is: n-(2-methyl-3-nitrophenyl) ethoxymethyl imine):n(potassium ethylate and diethyl oxalate)=1:1.05;

[0046] The crude 4-nitroindole was recrystallized from oxalic acid ethanol, the weight ratio ...

Embodiment 2

[0048] A kind of synthetic method of 4-nitroindole, main process parameter is:

[0049] With 2-methyl-3-nitroaniline and triethyl orthoformate under the catalysis of benzoic acid, react to generate N-(2-methyl-3-nitrophenyl) ethoxymethimine, benzoic acid The added amount is 10% of the amount of 2-methyl-3 nitroaniline substance;

[0050] The molar mass ratio of 2-methyl-3-nitroaniline to triethyl orthoformate is 0.9:1;

[0051] N-(2-methyl-3-nitrophenyl) ethoxymethanimine reacts with sodium ethylate and diethyl oxalate to generate 4-nitroindole crude product;

[0052] The molar ratio of sodium ethylate and diethyl oxalate is n (sodium ethylate):n (diethyl oxalate)=1.1:1;

[0053] The molar ratio of 2-methyl-3-nitrophenyl) ethoxymethylimine to potassium ethoxide and diethyl oxalate is: n-(2-methyl-3-nitrophenyl) ethoxymethyl imine):n(potassium ethylate and diethyl oxalate)=1:1.05;

[0054] The crude 4-nitroindole was recrystallized from oxalic acid ethanol, the weight ratio...

Embodiment 3

[0056] A kind of synthetic method of 4-nitroindole, main process parameter is:

[0057] With 2-methyl-3-nitroaniline and triethyl orthoformate under the catalysis of benzoic acid, react to generate N-(2-methyl-3-nitrophenyl) ethoxymethimine, benzoic acid The added amount is 7% of the amount of 2-methyl-3 nitroaniline substance;

[0058] The molar mass ratio of 2-methyl-3-nitroaniline to triethyl orthoformate is 1:1;

[0059] N-(2-methyl-3-nitrophenyl) ethoxymethanimine reacts with sodium ethylate and diethyl oxalate to generate 4-nitroindole crude product;

[0060] The molar ratio of sodium ethylate and diethyl oxalate is n (sodium ethylate):n (diethyl oxalate)=1.2:1;

[0061] The molar ratio of 2-methyl-3-nitrophenyl) ethoxymethylimine to potassium ethoxide and diethyl oxalate is: n-(2-methyl-3-nitrophenyl) ethoxymethyl imine):n(potassium ethylate and diethyl oxalate)=1:1.1;

[0062] The crude 4-nitroindole was recrystallized from oxalic acid ethanol, the weight ratio of ...

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Abstract

The invention discloses a synthesis method of 4-nitroindole, and belongs to the field of chemical synthesis. N-(2-methyl-3-nitrophenyl)ethyoxyl azomethine is generated after 2-methyl-3-nitroaniline and existing triethyl ester react under the catalysis of benzoic acid at the temperature of 100 DEG C for 1.5-2 hours, N-(2-methyl-3-nitrophenyl)ethyoxyl azomethine, sodium ethoxide and diethyl oxalate react at the temperature of 40 DEG C for 1.5 hours to generate a 4-nitroindole rough product, and recrystallization and sublimation reaction are conducted on the 4-nitroindole rough product to obtain 4-nitroindole. By means of the method, on the basis of the prior art, process parameters are optimized one by one, the total yield of reaction is increased, reaction time is shortened, and synthesis economic benefits are improved.

Description

Technical field: [0001] The invention relates to a synthesis method of 4-nitroindole, which belongs to the field of chemical synthesis. Background technique: [0002] 4-Nitroindole is an important intermediate for preparing other simple 4-substituted indoles, and is also an important raw material for the synthesis of dyes and drugs. About the synthesis method of 4-nitroindole, there are few domestic relevant literature reports, and there are many foreign studies: such as the synthesis of 4-nitroindole through 2-methyl-3-nitroaniline ring closure, the synthesis of 4-nitroindole through m-nitrophenylhydrazone Hydrolysis after cyclization to produce 4-nitroindole, 4-nitroindole through m-dinitrobenzene derivatives, 4-nitroindole through 4-nitroindoline, etc. However, what is valuable in the above-mentioned method for synthesizing 4-nitroindole is to use 2-methyl-3-nitroaniline as a starting material to prepare 4-nitroindole by alkali induction under the promotion of dialkyl ox...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D209/08
CPCC07D209/08
Inventor 胡海威丁靓闫永平郑辉严辉
Owner SUZHOU RYAN PHARMACHEM TECH CO LTD