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4-methyl-2-nitroaniline synthesis method

A technology of nitroaniline and methylaniline, which is applied in the field of clean preparation of organic chemicals, can solve the problems of high requirements for equipment and synthesis process conditions, strict process control requirements, and large environmental damage, so as to facilitate industrial production, The effect of clean reaction process and simple post-reaction treatment

Inactive Publication Date: 2018-03-06
NANJING UNIV OF SCI & TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0005] However, its process control requirements are relatively strict
[0006] 3. The third route also has high requirements on equipment and synthesis process conditions, as well as problems such as the source of raw materials
[0007] 4. Most of the nitrating agents used in the first and second are nitric acid, which is highly corrosive, causes great damage to equipment, and causes great damage to the environment

Method used

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  • 4-methyl-2-nitroaniline synthesis method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0024] Simply condense 4-methylaniline with ethyl chloroformate for amino protection to generate N-(p-toluene) ethyl carbamate, and then add 0.10 N-(p-toluene) ethyl carbamate to a 35.0 mL pressure-resistant tube mmol, 0.01 mmol of copper sulfate, 0.60 mmol of tert-butyl nitrite, 2 mL of 1,4-dioxane, using air as oxidant, placed in an oil bath and heated to 90 °C; TLC monitored the reaction (V 乙酸乙酯 : V 石油醚 = 1:10); after reacting for 6 h, extract the organic phase with ethyl acetate, combine the organic phases, wash with water (3×10 mL), dry over anhydrous sodium sulfate, filter with suction, obtain the crude product after vacuum distillation, use Ethyl acetate:petroleum ether=1:20 mixed organic solvent was the eluent, purified with silica gel column, and then hydrolyzed to obtain the target product; the final yield was 70%. 1 H NMR (300 MHz, CDCl 3 ) δ 9.71 (s, 1H), 8.44 (d, J = 8.7 Hz, 1H), 8.00 (s, 1H), 7.45 (d, J = 9.9 Hz, 1H), 4.26 (q, J = 7.1 Hz, 2H), 2.38 (s,3...

Embodiment 2

[0026] In a 35.0 mL pressure-resistant tube, add 0.10 mmol of N-(p-toluene) ethyl carbamate, 0.01 mmol of copper chloride, 0.60 mmol of tert-butyl nitrite, 2 mL of 1,4-dioxane, and use air as the oxidant , placed in an oil bath, the reaction was heated up to 90°C; TLC monitored the reaction (V 乙酸乙酯 :V 石油醚 = 1:10); after reacting for 6 h, extract the organic phase with ethyl acetate, combine the organic phases, wash with water (3 × 10 mL), dry over anhydrous sodium sulfate, filter with suction, obtain the crude product after distillation under reduced pressure, use Ethyl acetate:petroleum ether=1:20 mixed organic solvent was used as eluent, purified by silica gel column, and then hydrolyzed to obtain the target product; the final yield was 79%.

Embodiment 3

[0028] In a 35.0 mL pressure-resistant tube, add 0.10 mmol of N-(p-toluene) ethyl carbamate, 0.01 mmol of copper nitrate, 0.60 mmol of tert-butyl nitrite, 2 mL of 1,4-dioxane, and use air as the oxidant. Place the reaction in an oil bath and heat up to 90°C; TLC monitors the reaction (V 乙酸乙酯 :V 石油醚 = 1:10); after reacting for 6 h, extract the organic phase with ethyl acetate, combine the organic phases, wash with water (3 × 10 mL), dry over anhydrous sodium sulfate, filter with suction, obtain the crude product after distillation under reduced pressure, use Ethyl acetate:petroleum ether=1:20 mixed organic solvent was used as eluent, purified by silica gel column, and then hydrolyzed to obtain the target product; the final yield was 74%.

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Abstract

The invention discloses a 4-methyl-2-nitroaniline synthesis method, which comprises: carrying out amino protection with ethyl chloroformate by using 4-methylaniline as a raw material to generate N-(p-toluene)ethyl carbamate; adding an oxidant and a copper salt catalyst, and carrying out a reaction for a certain time at a temperature of 50-120 DEG C in a reaction solvent by using a nitroso-containing compound as a nitrating agent to prepare a corresponding protected o-nitro-p-toluidine; and carrying out hydrolysis to obtain the target product. According to the present invention, the method hasadvantages of simple preparation process, mild reaction condition, high yield and environment protection.

Description

technical field [0001] The invention relates to a new method for synthesizing 4-methyl-2-nitroaniline, which belongs to the field of clean preparation of organic chemicals. Background technique [0002] 4-methyl-2-nitroaniline, also known as red base GL, GL base or oil red base. It is an important intermediate. It is mainly used in the synthesis of organic pigments, such as toluidine red, toluidine purple, etc.; it can also be used as a dye, and it can be used as a developer for cotton and viscose dyeing and printing in combination with naphthol in ice dyeing dyes. There are many synthetic methods of 4-methyl-2-nitroaniline. According to the different acylating agents, nitrating agents, solvents, hydrolysis methods and raw materials used in it, there are many different synthetic methods, but generally speaking, There are three main routes 。 The first is the sulfonylation route: using 4-methylaniline and p-toluenesulfonyl chloride as the main raw materials, it is formed th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C209/62
CPCC07C209/62C07C269/04C07C269/06C07C211/52C07C271/28
Inventor 彭新华胡传峰高曦黄志达傅惠惠
Owner NANJING UNIV OF SCI & TECH
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