6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]-pyridine-3-acetic acid synthesis
- Product Name:6-Methyl-2-(4-methylphenyl)imidazol[1,2-a]-pyridine-3-acetic acid
- CAS Number:189005-44-5
- Molecular formula:C17H16N2O2
- Molecular Weight:280.32
79-37-8
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88965-00-8
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189005-44-5
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Yield:189005-44-5 95.2%
Reaction Conditions:
Stage #1:oxalyl dichloride;6-methyl-2-(4-methyl-phenyl)-imidazo[1,2-a]pyridine with potassium carbonate in tetrahydrofuran at 20 - 35;
Stage #2: with potassium hydroxide in tetrahydrofuran;water at 65 - 70;
Stage #3: with hydrazine hydrate in water at 110 - 115;Reagent/catalyst;Temperature;Solvent;
Steps:
1
0.15 mol of compound I and 160 ml of tetrahydrofuran are stirred at 20 to 35 ° C. To the stirred solution, 0.30 mol of potassium carbonate is added, and 0.30 mol of oxalyl chloride is slowly added. The reaction mixture was stirred at 20-35 ° C for 2-3 h and the reaction was monitored by TLC. The spots were single and the reaction was complete.
Slowly add 350 ml of 0.37 mol potassium hydroxide aqueous solution. The temperature was raised to 65 to 70 ° C and tetrahydrofuran was distilled off. Add 0.30mol of potassium hydroxide and 0.23mol of 50% hydrazine hydrate aqueous solution, heated to 110 ~ 115 , the reaction 14 ~ 16h. The reaction was monitored by TLC, the reaction was complete, cooled to 40 ° C, filtered after addition of 250 ml of water. Continue to cool to 5 ~ 15 , a mixed solution of 0.89mol acetic acid and 10ml methanol was added to the filtrate, stirred and filtered, and dried to obtain the compound V 48.02g, yield 95.2%, purity 99.6%.
References:
Jiangsu Haosen Pharmaceutical Group Co., Ltd.;Yang Baohai;Chen Gangsheng;Li Xiaobi;Sun Changan CN106749237, 2017, A Location in patent:Paragraph 0046-0096
193979-47-4
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82626-48-0
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1603-41-4
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