With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.67367-24-2, name is Methyl 4-hydroxynicotinate, molecular formula is C7H7NO3, molecular weight is 153.1354, as common compound, the synthetic route is as follows.Safety of Methyl 4-hydroxynicotinate
A solution of the required alcohol (0.30 mmol; 3 eq.) in DMF (0.2 mL), in a glass vial under inert atmosphere (N2), is treated with NaH (3.3 eq.) at rt. After 10 min, it is treated with a solution of the chloride (0.10 mmol; 1 eq.) in DMF (0.8 mL) and the reaction mixture is stirred at rt and monitored by LC-MS. Upon reaction completion, the reaction mixture is either treated with silica gel-supported sulfonic acid (5.0 eq.; Silicycle SiliaBond Tosic Acid; SCX; R60530B; 0.8 mmol/g), shaken 1 h at rt and filtered, or loaded on a corresponding cartridge (Silicycle SiliaPrep Tosic Acid Si-SCX). In both cases, the resin is then washed with DCM, 1:1 DCM/MeOH and MeOH, and the product eventually released from the resin with 7M ammonia solution in MeOH. The solution of crude product is concentrated under reduced pressureand purification of the residue gives the desired product.Example 212 4-[3-(3-ethyl-ureido)-isoquinolin-8-ylmethoxy]-nicotinic acid methyl ester hydrochloride Starting from the compound of Preparation R and methyl 4-hydroxynicotinate and proceeding in analogy to Procedure AC, the title compound was obtained, after purification by prep-HPLC (acidic conditions) and treatment with HCl, as an amorphous solid (21% yield). MS (ESI, m/z): 381.28 [M+H+].
At the same time, in my other blogs, there are other synthetic methods of this type of compound,67367-24-2, Methyl 4-hydroxynicotinate, and friends who are interested can also refer to it.
Reference:
Patent; Bur, Daniel; Gude, Markus; Hubschwerlen, Christian; Panchaud, Philippe; US2013/96119; (2013); A1;,
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