Synthesis method of 2-chloro-3-amido-4picoline from cyanoacetamide and acetone

A technology of picoline method and cyanoacetamide, which is applied in the direction of organic chemistry, can solve the problems of high cost, long process route, and low total yield, and achieve the effect of less reaction steps, good selectivity, and mild reaction conditions

Inactive Publication Date: 2006-04-26
江阴暨阳医药化工有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The process route of this method is long, the environmental pollution is more serious, and the total yield is low
[0011] In summary, the above seven synthetic methods are too complicated, the yield is low, the selectivity conditions are difficult to control, and the cost is high

Method used

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  • Synthesis method of 2-chloro-3-amido-4picoline from cyanoacetamide and acetone
  • Synthesis method of 2-chloro-3-amido-4picoline from cyanoacetamide and acetone
  • Synthesis method of 2-chloro-3-amido-4picoline from cyanoacetamide and acetone

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Experimental program
Comparison scheme
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Embodiment 1

[0032] Step 1: Synthesis of Condensate I

[0033] Add 43.4g (0.5mol) of cyanoacetamide, 80ml of benzene, and 1.3g of piperidine into the reaction kettle, heat up to reflux, dropwise add a mixture of acetone (55g) and glacial acetic acid (9.6g), and reflux to separate water while adding dropwise. After the dropwise addition, continue to reflux and divide the water until all the water evaporates. After the reaction, the temperature was lowered to 25° C., and the layers were washed with 50 ml of water. The organic phase is adjusted to PH value to 8 ~ 9 with saturated sodium carbonate, static layering, the aqueous phase is extracted with 50ml benzene, the combined organic phase is washed once with saturated sodium chloride solution, and concentrated to dryness to obtain 54.5 grams of condensate I (content 91.3%, yield 80.2%). After cooling the condensate I, 20 g of methanol was added as a solvent.

[0034] Step 2: Synthesis of Condensate II

[0035] In a reaction kettle, under...

Embodiment 2

[0043]Change solvent benzene into toluene in the first step of embodiment 1, adjust pH value and replace with saturated sodium bicarbonate solution, other operating conditions (comprising aftertreatment step) are identical with embodiment 1. As a result, 55.5 g of condensate I was obtained (content 92.5%, yield 81.7%). All the other are with embodiment 1.

Embodiment 3

[0045] Change the logical hydrogen chloride gas reaction time into 20 hours in the third step of embodiment 1, change solvent toluene into benzene, and other operating conditions (comprising aftertreatment steps) are identical with embodiment 1. As a result, 44.2 grams of dry cyclized product was obtained (content 90.5%, yield 76.6%). All the other are with embodiment 1.

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Abstract

The present invention relates to the process of synthesizing 2-chloro-3-amino-4-methyl pyridine as one kind of intermediate for AIDS medicine Nevirapine with cyanoacetamide and acetone. The present invention features that cyanoacetamide and acetone as initial materials are prepared into 2-chloro-3-amino-4-methyl pyridine through condensation, cyclization and degradation. Compared with available technology, the present invention has the outstanding features of less reaction steps, mild reaction condition, high selectivity, high product yield up to 37 %, product purity over 99 % and being suitable for industrial production.

Description

technical field [0001] The present invention relates to a synthetic method of 2-chloro-3-amino-4-picoline, an intermediate of anti-AIDS drug nevirapine, in particular to a method for synthesizing 2-chloro-3-amino-4-methylpyridine with cyanoacetamide and acetone. 4-picoline method. It belongs to the technical field of organic chemical synthesis. Background technique [0002] 2-Chloro-3-amino-4-picoline is the key intermediate of the anti-AIDS drug Nevirapine. Nevirapine belongs to non-nucleoside reverse transcriptase inhibitors, which mainly prevent HIV replication and is used in combination with other reverse transcriptase inhibitors to treat HIV-1 infection. It is one of the most widely used anti-AIDS drugs and is mainly used to prevent mother-to-child virus transmission. Compared with other anti-AIDS drugs, nevirapine has strong antiviral effect, long half-life, high bioavailability, good tolerance and low cost. From the geographical distribution of AIDS incidence, the...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D213/73
Inventor 徐志远高桂祥邢友华
Owner 江阴暨阳医药化工有限公司
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