- Development of an improved and scalable process for 2-(5-ethylpyridin-2-yl) ethan-1-ol: Solvent-free reaction and recycling of the starting material 5-ethyl-2-picoline
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The main objective of this exercise was to develop a more efficient process for 2-(5-ethylpyridin-2-yl)ethan-1-ol (1), which is the key intermediate in the synthesis of pioglitazone hydrochloride. This process not only features the yield improvement of (1) by optimizing reaction variables in solvent-free conditions but also highlights improving the mass efficiency of 5-ethyl-2-picoline (2), thereby reducing the effluent load per kilogram of the intermediate.
- Mohanty, Sandeep,Talasila, Srinivasarao,Roy, Amrendra Kumar,Karmakar, Arun Chandra
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- 5-(4-HYDROXYBENZYL)THIAZOLIDINE-2,4-DIONE AS INTERMEDIATE FOR SYNTHESIS OF THIAZOLIDINEDIONE BASED COMPOUNDS AND PROCESS FOR PREPARING THE SAME
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The present invention relates to 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by the following Chemical Formula [1], which is useful as an intermediate for synthesis of thiazolidinedione based compounds, a method for preparing the compound, and a method for preparing pioglitazone or pioglitazone hydrochloride, which is a thiazolidinedione based drug and useful in treating and preventing diabetes, using the 5-(4-hydroxybenzyl)thiazolidine-2,4-dione represented by Chemical Formula [1] as an intermediate:
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(2009/12/28)
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- PROCESS FOR THE PREPARATION OF 5-[[4-[2-(5-ETHYL-2-PYRIDINYL)ETHOXY]PHENYL] METHYL]-2,4-THIAZOLIDINEDIONE
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A process for the preparation of 5-[[4-[2-(5-ethyl-2-pyridinyl)ethoxy]phenyl]methyl]-2,4-thiazolidinedione (formula 1) comprising a. reacting diazonium salt of 4-[2-(5-Ethyl-2-pyridyl) ethoxy] amino- benzene, compound of formula 2, with acrylamide, aqueous HX (wherein X is Br or Cl), under meerwein arylation conditions to yield compound of formula 3; b. condensing compound of formula 3 with thiourea to obtain compound of formula 4; and c. converting compound of formula 4 to compound of formula 1.
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- Production of benzaldehyde compounds
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A method of producing a compound represented by the formula: STR1 wherein R1 stands for hydrogen or an optionally substituted alkyl or acyl group, which comprises reacting a compound represented by the formula: STR2 wherein R1 is of the same meaning as defined above, and R2 stands for an optionally halolgenated alkyl group or an optionally substituted phenyl group with a compound represented by the formula: STR3 in a lower alcohol in the presence of an alkali metal or alkaline earth metal carbonate; the compound (III) being useful as starting compounds for producing thiazolidinedione derivatives having hypoglycemic and hypolipidemic activities.
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