CN101870653B - Synthesis method of 2 - methyl -3 - fluoride - 6 -nitrobenzoic acid - Google Patents
Synthesis method of 2 - methyl -3 - fluoride - 6 -nitrobenzoic acid Download PDFInfo
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- CN101870653B CN101870653B CN 200910057123 CN200910057123A CN101870653B CN 101870653 B CN101870653 B CN 101870653B CN 200910057123 CN200910057123 CN 200910057123 CN 200910057123 A CN200910057123 A CN 200910057123A CN 101870653 B CN101870653 B CN 101870653B
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Abstract
The invention relates to a synthesis method of important medicine midbody 2 - methyl -3 - fluoride - 6 -nitrobenzoic acid. The invention provides a novel synthesis route, which can rapidly and conveniently prepare an important medicine midbody from the cheap and facile raw materials. The process not only has high yield, but also is applicable to the mass production. The process method is started from 2 - methyl -3-fluoroaniline, crucial midbody N-(2-Methyl -3-- fluoride -6-nitrophenyl) acetamide is selectively generated through the nitration reaction, and the acetyl is hydrolyzed to obtain the 2 - methyl -3-- fluoride -6-nitroaniline; then the amidocyanogen has diazo reaction to generate 2 - bromo -3-- methyl -4-- F - nitrobenzene; bromide generates corresponding cyano compound under the effect of cuprous cyanide; and finally the 2 - methyl -3 - fluoride - 6 -nitrobenzoic acid is obtained under the effect of the sulfuric acid and the sodium nitrite.
Description
Technical field:
The present invention relates to the synthetic method of a kind of important medicine intermediate 2-methyl-3-fluoro-6-nitrobenzoic acid.
Background technology:
2-methyl-3-fluoro-6-nitrobenzoic acid is a kind of important medicine intermediate, and it can be used for synthesizing a lot of small-molecule drugs.The synthetic route of having only one piece of Japanese Patent (JP04295441) report related analogs at present.But its reaction yield is very low, and selectivity is also poor, and uses costliness, unsettled reagent.Two pieces of patents are arranged in addition, and (US2008293708A1, WO2006021457A2) report comes the synthesizing antineoplastic medicament molecule with 2-methyl-3-fluoro-6-nitrobenzoic acid, but does not indicate corresponding source.
Summary of the invention:
The object of the present invention is to provide the new synthetic method of a kind of important medicine intermediate 2-methyl-3-fluoro-6-nitrobenzoic acid, mainly solve aftertreatment complexity, separation and purification difficulty that existing synthetic method lacks and exists, technical problems such as productive rate is low, synthesizes the cost height, and suitability is wideless.
Technical scheme of the present invention: the synthetic method of a kind of 2-methyl-3-fluoro-6-nitrobenzoic acid, may further comprise the steps: be raw material with 2-methyl-3-fluoroaniline 1, optionally generate key intermediate N-(2-methyl-3-fluoro-6-nitrophenyl) ethanamide 2 by nitration reaction, obtain 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 after the ethanoyl hydrolysis; Then amido is generated 2-bromo-3-methyl-4-fluoro-oil of mirbane 4 through diazotization reaction; Bromo-derivative 4 generates corresponding cyano compound 5 under the cuprous cyanide effect; Under sulfuric acid and Sodium Nitrite effect, obtain 2-methyl-3-fluoro-6-nitrobenzoic acid 6 at last.Chemical equation is as follows:
Described nitration reaction is: 2-methyl-3-fluoroaniline 1 is mixed be dissolved in the diacetyl oxide, dripping weight percents at-10 ℃ is 65% nitric acid, and reaction is 16 hours under the room temperature.Recrystallization obtains N-(2-methyl-3-fluoro-6-nitrophenyl) ethanamide 2 in ethanol.
Second one-step hydrolysis reacts for N-(2-methyl-3-fluorophenyl) ethanamide 2 is dissolved in ethanol and the concentrated hydrochloric acid, heats to obtain 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 in 10～24 hours.
The 3rd step diazotization reaction is 48% hydrobromic acid solution for 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 being dissolved in weight percent, drips sodium nitrite in aqueous solution down at 0 ℃, 0 ℃ of reaction 30 minutes down, is added drop-wise in the mixed solution of cuprous bromide and water earlier.Obtained 2-bromo-3-methyl-4-fluoro-oil of mirbane 4 in 1～5 hour 60～100 ℃ of reactions.
Four-step reaction in the dinethylformamide, adds cuprous cyanide for 2-bromo-3-methyl-4-fluoro-oil of mirbane 4 is dissolved in N, reacts down at 100～150 ℃ to obtain 2-methyl-3-fluoro-6-p-nitrile 5 in 10～24 hours.
The reaction of the 5th step is to react 10～24 hours under 80～120 ℃ in 40～80% sulfuric acid for 2-methyl-3-fluoro-6-p-nitrile 5 being dissolved in weight percent, and reaction obtained 2-methyl-3-fluoro-6-nitrobenzoic acid 6 in 1 hour under the Sodium Nitrite effect then.
The invention has the beneficial effects as follows: the invention provides a kind of synthetic route of novelty, can prepare a kind of important medicine intermediate quickly and easily from raw material cheap, that be easy to get.This process yield can reach 80%, and it is synthetic to be fit to large-scale industry.
Embodiment:
Following example helps to understand content of the present invention, the present invention includes but is not limited to following related content:
Embodiment 1
1.N-(2-methyl-3-fluoro-6-nitrophenyl) ethanamide 2 is synthetic
(600g 4.8mol) is dissolved in diacetyl oxide (3000mL) to 2-methyl-3-fluoroaniline 1, then solution is cooled to-10 ℃, and the concentrated nitric acid (375mL) with weight percent 65% under this temperature slowly is added drop-wise in the reaction solution.After 3 hours, dropwise, reaction solution is raised to room temperature naturally, stirs then 16 hours.The solid filtering of separating out in the reaction solution obtains the 250g product.Mother liquor concentrates the dried thick product that obtains again, obtains the pure product N-of other 550g (2-methyl-3-fluoro-6-nitrophenyl) ethanamide 2 with ethyl alcohol recrystallization.(yield: 78%).
Proton nmr spectra
1H-NMR (DMSO, 400MHz), δ ppm:9.99 (s, 1H), 7.82 (dd, J
1=8.8Hz, J
2=5.6Hz, 1H), 6.50 (t, J=8.8Hz, 1H), 2.12 (s, 3H), 2.02 (s, 3H).
2.2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 is synthetic
(500g 2.4mol) is dissolved in the mixing solutions of 2000mL concentrated hydrochloric acid and 2000mL ethanol, the reaction solution heating with N-(2-methyl-3-fluoro-6-nitrophenyl) ethanamide 2.Stirred then 12 hours.Reaction solution is concentrated into 2000mL, and then with saturated aqueous sodium carbonate neutralization, the pH value is by 9 o'clock, and mixing solutions is with the ethyl acetate extraction of 2000mL three times.The organic phase anhydrous sodium sulfate drying that merges.After the siccative filtration, filtrate concentrating obtains product 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 (productive rates: 90%) of 360g
Proton nmr spectra
1H-NMR (DMSO, 400MHz), δ ppm:7.96 (dd, J
1=8.8Hz, J
2=5.6Hz, 1H), 7.35 (br s, 2H), 6.50 (t, J=8.8Hz, 1H), 2.04 (s, 3H).
3.2-bromo-3-methyl-4-fluoro-oil of mirbane 4 is synthetic
(200g 1.2mol) is dissolved in the hydrobromic acid solution of 1000mL weight percent 48% with 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3.Under 0 ℃, slowly drip Sodium Nitrite (100g, aqueous solution 1.4mol) (600mL).Dropwise, reaction solution was stirred 30 minutes down at 0 ℃.(200g, 1.4mol) and water (2000mL), with mixture heating up to 70 ℃, the diazonium salt that will before prepare slowly drops in the mixture of cuprous bromide under this temperature then to add cuprous bromide in the another one reaction flask.Deng dropwising, reaction solution continues to stir 3 hours.Reaction solution is cooled to room temperature, and then with saturated aqueous sodium carbonate neutralization, the pH value is by 9 o'clock, and mixing solutions is with the ethyl acetate extraction of 3000mL three times.The organic phase anhydrous sodium sulfate drying that merges.After the siccative filtration, filtrate concentrates the dried thick product that obtains.Column chromatography for separation obtains the pure product 2-of 170g bromo-3-methyl-4-fluoro-oil of mirbane 4 (productive rates: 61%)
Proton nmr spectra
1H-NMR (DMSO, 400MHz), δ ppm:7.86 (dd, J
1=8.8Hz, J
2=5.6Hz, 1H), 7.41 (t, J=8.8Hz, 1H), 2.25 (s, 3H).
4.2-methyl-3-fluoro-6-p-nitrile 5 is synthetic
With 2-bromo-3-methyl-4-fluoro-oil of mirbane 4 (120g, 0.51mol) and cuprous cyanide (120g, 1.33mol) at the N of 1000mL, dinethylformamide solution is heated to 150 ℃, stirs under this temperature 12 hours then.Reaction solution concentrates the dried thick product that obtains, and column chromatography for separation obtains the pure product 2-methyl of 60g-3-fluoro-6-p-nitrile 5 (productive rates: 65%)
Proton nmr spectra
1H-NMR (DMSO, 400MHz), δ ppm:8.29 (dd, J
1=8.8Hz, J
2=5.6Hz, 1H), 7.41 (t, J=8.8Hz, 1H), 2.46 (s, 3H).
5.2-methyl-3-fluoro-6-nitrobenzoic acid 6 is synthetic
After the water of the 100mL vitriol oil and 100mL mixed, add 2-methyl-3-fluoro-6-p-nitrile 5 (50g, 0.28mol).Reaction solution stirred 14 hours at 100 ℃.After thin-layer chromatography detection raw material consumption is intact, reaction solution is cooled to 0 ℃, slowly drip Sodium Nitrite (62.5g, aqueous solution 0.9mol) (100mL) then.Dropwise, reaction solution stirred 30 minutes down at 0 ℃, was heated to 90 ℃ then, and reaction solution stirred 1 hour under this temperature.After reaction solution water (1000mL) dilution, the ethyl acetate extraction of mixing solutions usefulness 2000mL three times.The organic phase anhydrous sodium sulfate drying that merges.After the siccative filtration, filtrate concentrates the dried pure product 2-methyl of the 45g-3-fluoro-6-nitrobenzoic acid 6 (productive rates: 80%) that obtain
Proton nmr spectra
1H-NMR (DMSO, 400MHz), δ ppm:8.10 (dd, J
1=8.8Hz, J
2=5.6Hz, 1H), 7.45 (t, J=8.8Hz, 1H), 2.36 (s, 3H); MS (ESI) m/e (M
-) 198.
Embodiment 2
Second one-step hydrolysis reacts for N-(2-methyl-3-fluorophenyl) ethanamide 2 is dissolved in ethanol and the concentrated hydrochloric acid, heats to obtain 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 in 15 hours.
The 3rd step diazotization reaction is 48% hydrobromic acid solution for 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 being dissolved in weight percent, drips sodium nitrite in aqueous solution down at 0 ℃, 0 ℃ of reaction 30 minutes down, is added drop-wise in the mixed solution of cuprous bromide and water earlier.Obtained 2-bromo-3-methyl-4-fluoro-oil of mirbane 4 in 2 hours 80 ℃ of reactions.
Four-step reaction in the dinethylformamide, adds cuprous cyanide for 2-bromo-3-methyl-4-fluoro-oil of mirbane 4 is dissolved in N, reacts down at 130 ℃ to obtain 2-methyl-3-fluoro-6-p-nitrile 5 in 17 hours.
The reaction of the 5th step is to react 18 hours under 90 ℃ in 80% sulfuric acid for 2-methyl-3-fluoro-6-p-nitrile 5 being dissolved in weight percent, and reaction obtained 2-methyl-3-fluoro-6-nitrobenzoic acid 6 in 1 hour under the Sodium Nitrite effect then.
All the other are identical with embodiment 1.
Embodiment 3
Second one-step hydrolysis reacts for N-(2-methyl-3-fluorophenyl) ethanamide 2 is dissolved in ethanol and the concentrated hydrochloric acid, heats to obtain 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 in 18 hours.
The 3rd step diazotization reaction is 48% hydrobromic acid solution for 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline 3 being dissolved in weight percent, drips sodium nitrite in aqueous solution down at 0 ℃, 0 ℃ of reaction 30 minutes down, is added drop-wise in the mixed solution of cuprous bromide and water earlier.Obtained 2-bromo-3-methyl-4-fluoro-oil of mirbane 4 in 1 hour 100 ℃ of reactions.
Four-step reaction in the dinethylformamide, adds cuprous cyanide for 2-bromo-3-methyl-4-fluoro-oil of mirbane 4 is dissolved in N, reacts down at 110 ℃ to obtain 2-methyl-3-fluoro-6-p-nitrile 5 in 20 hours.
The reaction of the 5th step is to react 12 hours under 110 ℃ in 60% sulfuric acid for 2-methyl-3-fluoro-6-p-nitrile 5 being dissolved in weight percent, and reaction obtained 2-methyl-3-fluoro-6-nitrobenzoic acid 6 in 1 hour under the Sodium Nitrite effect then.
All the other are identical with embodiment 1.
Claims (6)
1. the synthetic method of 2-methyl-3-fluoro-6-nitrobenzoic acid, may further comprise the steps: be raw material with 2-methyl-3-fluoroaniline, optionally generate key intermediate N-(2-methyl-3-fluoro-6-nitrophenyl) ethanamide by nitration reaction, obtain 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline after the ethanoyl hydrolysis; Then amido is generated 2-bromo-3-methyl-4-fluoro-oil of mirbane through diazotization reaction; 2-bromo-3-methyl-4-fluoro-oil of mirbane generates corresponding cyano compound under the cuprous cyanide effect; Under sulfuric acid and Sodium Nitrite effect, obtain 2-methyl-3-fluoro-6-nitrobenzoic acid at last.
2. the synthetic method of a kind of 2-methyl according to claim 1-3-fluoro-6-nitrobenzoic acid, it is characterized in that, described nitration reaction is: 2-methyl-3-fluoroaniline mixing is dissolved in the diacetyl oxide, dripping weight percents at-10 ℃ is 65% nitric acid, reaction is 16 hours under the room temperature, and recrystallization obtains N-(2-methyl-3-fluoro-6-nitrophenyl) ethanamide in ethanol.
3. the synthetic method of a kind of 2-methyl according to claim 1-3-fluoro-6-nitrobenzoic acid, it is characterized in that, second one-step hydrolysis reacts for N-(2-methyl-3-fluorophenyl) ethanamide is dissolved in ethanol and the concentrated hydrochloric acid, heats to obtain 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline in 10～24 hours.
4. the synthetic method of a kind of 2-methyl according to claim 1-3-fluoro-6-nitrobenzoic acid, it is characterized in that, the 3rd step diazotization reaction is 48% hydrobromic acid solution for 2-methyl-3-fluoro-6-N-methyl-p-nitroaniline being dissolved in weight percent, drip sodium nitrite in aqueous solution down at 0 ℃, reacted 30 minutes down at 0 ℃ earlier, be added drop-wise in the mixed solution of cuprous bromide and water, obtained 2-bromo-3-methyl-4-fluoro-oil of mirbane in 1～5 hour 60～100 ℃ of reactions.
5. the synthetic method of a kind of 2-methyl according to claim 1-3-fluoro-6-nitrobenzoic acid, it is characterized in that, four-step reaction is for to be dissolved in N with 2-bromo-3-methyl-4-fluoro-oil of mirbane, in the dinethylformamide, add cuprous cyanide, reaction obtained 2-methyl-3-fluoro-6-p-nitrile in 10～24 hours under 100～150 ℃.
6. the synthetic method of a kind of 2-methyl according to claim 1-3-fluoro-6-nitrobenzoic acid, it is characterized in that, the reaction of the 5th step is to react 10～24 hours under 80～120 ℃ in 40～80% sulfuric acid for 2-methyl-3-fluoro-6-p-nitrile being dissolved in weight percent, and reaction obtained 2-methyl-3-fluoro-6-nitrobenzoic acid in 1 hour under the Sodium Nitrite effect then.
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| CN104387276B (en) * | 2014-12-01 | 2016-08-17 | 黑龙江格林赫思生物科技有限公司 | A kind of 2,4, the preparation method of 6-trimethoxy Nitrobenzol |
| TWI734776B (en) * | 2016-05-09 | 2021-08-01 | 日商組合化學工業股份有限公司 | Method for manufacturing nitrobenzene compound |
| CN108558672B (en) * | 2018-06-21 | 2021-04-30 | 利尔化学股份有限公司 | Preparation method of 2-nitro-4-trifluoromethylbenzoic acid and isomer thereof |
| CN111018740B (en) * | 2019-12-20 | 2022-04-05 | 阿里生物新材料（常州）有限公司 | Synthesis method of 4-bromo-2-cyano-5-fluorobenzoic acid methyl ester |
| CN111848446B (en) * | 2020-08-21 | 2022-03-11 | 阿里生物新材料（常州）有限公司 | Synthesis method of 2-bromo-5-cyano-4-fluorobenzoic acid methyl ester |
| CN112110824B (en) * | 2020-09-17 | 2023-04-07 | 上海凌凯医药科技有限公司 | Method for preparing 2-bromo-5-fluoroaniline |
| CN115594608A (en) * | 2022-10-20 | 2023-01-13 | 九江善水科技股份有限公司（Cn） | Preparation method of chlorantraniliprole intermediate |
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| WO2007115947A1 (en) * | 2006-04-06 | 2007-10-18 | Glaxo Group Limited | Pyrrolo-quinoxalinone derivatives as antibacterials |
| EP2041145A1 (en) * | 2006-07-03 | 2009-04-01 | Glaxo Group Limited | Azatricyclic compounds and their use |
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| WO2003004488A1 (en) * | 2001-07-03 | 2003-01-16 | Chiron Corporation | Indazole benzimidazole compounds as tyrosine and serine/threonine kinase inhibitors |
| WO2007115947A1 (en) * | 2006-04-06 | 2007-10-18 | Glaxo Group Limited | Pyrrolo-quinoxalinone derivatives as antibacterials |
| EP2041145A1 (en) * | 2006-07-03 | 2009-04-01 | Glaxo Group Limited | Azatricyclic compounds and their use |
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