Selective reduction method for nitro

A selective, nitro-based technology, applied in chemical instruments and methods, preparation of amino compounds, preparation of organic compounds, etc., can solve problems such as difficult separation, strong taste, and slow addition

Inactive Publication Date: 2015-03-11
NANJING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Among them, the nitro group reduction of compound 2 is mainly carried out by using sodium sulfide nonahydrate, which has a strong taste, slow feeding, and the risk of flushing.
However, the nitro reduction of compound 6 uses stannous chloride, the reaction waste acid is too much and the solution is easy to emulsify and difficult to separate

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] Embodiment 1: the synthesis of 2-methylamino-5-nitroaniline (compound 4)

[0010]

[0011] 5.0 g of 2,4-dinitro-N-methylaniline (compound 3) was dissolved in 30 mL of acetonitrile, and 0.5 g of palladium carbon (water content 48%) was added, then the temperature was lowered to -10°C, and formic acid was added dropwise to the acetonitrile Solution (5mL of formic acid was added to 10mL of acetonitrile to configure). After the dropwise addition was completed, the temperature was raised to reflux for 3 hours, and the filtrate was collected by filtration. The filtrate was poured into 50 mL of ice-pure water, stirred, and after the substance was completely precipitated, it was filtered to obtain 2.9 g of the precipitate (compound 4), with a yield of 68.4%.

Embodiment 2

[0012] Embodiment 2: the synthesis of 2-methylamino-5-nitroaniline (compound 4)

[0013] 5.0 g of 2,4-dinitro-N-methylaniline (compound 3) was dissolved in 30 mL of acetonitrile, and 0.5 g of palladium carbon (water content 48%) was added, then the temperature was lowered to -20°C, and formic acid was added dropwise to the acetonitrile solution (5mL of formic acid was added to 5mL of acetonitrile to configure). After the dropwise addition was completed, the temperature was raised to reflux for 3 hours, and the filtrate was collected by filtration. The filtrate was poured into 50 mL of ice-cold pure water, stirred, and filtered to obtain 30.5 g of the precipitate (compound 4), with a yield of 71.9%.

Embodiment 3

[0014] Embodiment 3: the synthesis of 2-methylamino-5-nitroaniline (compound 4)

[0015] 5.0 g of 2,4-dinitro-N-methylaniline (compound 3) was dissolved in 25 mL of acetonitrile, and 0.375 g of palladium carbon (water content 48%) was added, then the temperature was lowered to -30°C, and formic acid was added dropwise to the acetonitrile solution (5mL of formic acid was added to 5mL of acetonitrile to configure). After the dropwise addition was completed, the temperature was raised to reflux for 3 hours, and the filtrate was collected by filtration. The filtrate was poured into 62.5 mL of ice-cold pure water, stirred, and filtered to obtain 123.2 g of the precipitate (compound 4), with a yield of 72.6%.

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Abstract

The invention relates to an intermediate compound of bendamustine hydrochloride obtained by selective reduction of polynitro compound. The method uses an active hydrogen donor under palladium-carbon catalysis, then the active hydrogen donor is gradually added in reduced amino ortho nitro to obtain the corresponding compound. The compound can conveniently synthesize bendamustine hydrochloride through the method in the invention.

Description

technical field [0001] The invention relates to introducing a method for selectively reducing nitro groups to amino groups, using different reducing agents to reduce multiple nitro groups in reactants. Background technique [0002] Bendamustine Hydrochloride (Bendamustine Hydrochloride, Compound 1) is a drug developed by Cephalon Corporation of the United States for the treatment of chronic lymphocytic leukemia. It can be used to treat breast cancer, multiple myeloma, and indolent B-cell non-Hodgkin's lymphoma. etc. (Wang Xiaokun, Qilu Pharmaceutical Affairs, 2009, 28(9), 573-574; Chen Dong, Chinese Journal of Medicinal Chemistry 2009, 19(2) 159-160). [0003] Its chemical synthesis mostly starts with 2,4-dinitrochlorobenzene (compound 2), and obtains bendamustine hydrochloride through different modifications to the selective reduction of two nitro groups (Gao Limei, Wang Yanxiang, Song et al. Danqing, Chinese Journal of New Drugs, 2007, 16(23)1960-1961; Ren Jian, Chinese J...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C211/52C07C209/36C07C233/43C07C231/02C07D235/16
Inventor 张远莉
Owner NANJING UNIV
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