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Preparation process of p-nitro phenyl hydrazine hydrochloride

A technology of nitrophenylhydrazine and p-chloronitrobenzene, which is applied in the preparation of hydrazine, organic chemistry, etc., can solve the problems of long reaction steps, low product yield, and high raw material price, and achieve low cost, good product purity, and high yield. high rate effect

Inactive Publication Date: 2007-07-18
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] The technical problem solved by the present invention is to provide a preparation method of p-nitrophenylhydrazine hydrochloride to overcome the shortcomings of long reaction steps, high raw material prices, low product yield, high preparation cost and cumbersome operation in the prior art

Method used

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  • Preparation process of p-nitro phenyl hydrazine hydrochloride
  • Preparation process of p-nitro phenyl hydrazine hydrochloride
  • Preparation process of p-nitro phenyl hydrazine hydrochloride

Examples

Experimental program
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Embodiment 1

[0021] Add 150ml chloroform, 78.8g (0.5mol) p-chloronitrobenzene respectively in the 500ml reaction bottle that has stirrer, thermometer, reflux condenser, stir and dissolve at room temperature, add 100ml water under stirring, 34.4g (0.55mol) 80 % hydrazine hydrate, 1.2 g 18-crown-6 and 1.2 g sodium fluoride were added. Heat up, react at 50-55°C for 4.5 hours, cool the reaction solution to room temperature, let stand to separate the organic phase, evaporate chloroform under reduced pressure, add 45ml of 37% hydrochloric acid and 150ml of 95% ethanol to the obtained p-nitrophenylhydrazine, and stir While gradually heating up to 70°C, and cooling down to 0-5°C after complete dissolution, the filtered solid was dried to obtain 78.3g of p-nitrophenylhydrazine hydrochloride orange-red needle crystals, with a yield of 82.6% and a purity of 99.3%. (HPLC), melting point 204-205°C.

Embodiment 2

[0023] Add 160ml of 1,2-dichloroethane and 78.8g (0.5mol) p-chloronitrobenzene respectively in a 500ml reaction flask with a stirrer, a thermometer, and a reflux condenser, stir and dissolve at room temperature, add 120ml of water under stirring, 36.3 g (0.58mol) 80% hydrazine hydrate, add 1.4g 15-crown-5 and 1.4g potassium fluoride. Heating and raising the temperature, reacting at 55-60°C for 5 hours, cooling the reaction liquid to room temperature, standing to separate the organic phase, distilling off 1,2-dichloroethane under reduced pressure, adding 45ml of 37% hydrochloric acid to the obtained p-nitrophenylhydrazine, In 150ml of 95% ethanol, gradually heat up to 70°C while stirring, cool down to 5-10°C after completely dissolving, and dry the filtered solid to obtain 80.4g of p-nitrophenylhydrazine hydrochloride orange-red needle crystals. The yield is 84.8%, the purity is 99.4% (HPLC), and the melting point is 204.5-205°C.

[0024] With the same method in the foregoing ...

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Abstract

The invention relates to a p-Nitrophenylhydrazine muriate preparation methods. In halogenated hydrocarbonand water two-phase system, take p-cl-nitrobenzene as raw material to take reaction with hydrazine hydrate under catalyst, obtain p-Nitrophenylhydrazine, then through hydrochloride to obtain product of the invention. With this method, the purity of p-Nitrophenylhydrazine muriate can achieve more than 99%, 80 to 85% yield.

Description

technical field [0001] The invention relates to a preparation method of a pharmaceutical intermediate p-nitrophenylhydrazine hydrochloride. Background technique [0002] p-Nitrophenylhydrazine hydrochloride is an important fine chemical raw material, especially as a pharmaceutical intermediate for synthetic drugs. Its structural formula is: [0003] [0004] Chem.-Ztg 42, 112-15 (1939) in the prior art; "A Textbook of Practical Organic Chemistry", 4th ed., London, 728, 1978. It is reported that take p-nitroaniline as raw material, through diazotization reaction , sodium sulfite reduction, hydrochloric acid hydrolysis, prepare the synthetic method of nitrophenylhydrazine hydrochloride, yield 63-72%, in the above-mentioned preparation method, take p-nitroaniline as raw material, through diazotization, reduction, hydrochloric acid hydrolysis The preparation method has long reaction steps, cumbersome operation, low yield and high cost; the former Soviet patent SU 1,616,904 r...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C243/22C07C241/02
Inventor 揭元萍施险峰蒋旭亮
Owner SHANGHAI CHEM REAGENT RES INST
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