The origin of a common compound about 6-Methoxynicotinaldehyde

Statistics shows that 65873-72-5 is playing an increasingly important role. we look forward to future research findings about 6-Methoxynicotinaldehyde.

Synthetic Route of 65873-72-5, 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.65873-72-5, name is 6-Methoxynicotinaldehyde, molecular formula is C7H7NO2, molecular weight is 137.14, as common compound, the synthetic route is as follows.

Reference Example 28Step 15-chloromethyl-2-methoxypyridine (Compound A80)2-methoxy-5-pyridinecarbaldehyde (137 mg, 0.999 mmol) was dissolved in methanol (5.0mL). To this, sodium borohydride (37.8 mg, 0.999 mmol) was added at 0C, and the mixture was stirred for 1 hour. To the reaction mixture, a saturated ammonium chloride aqueous solution was added, and extraction with ethyl acetate was performed twice. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the residue was dissolved in dichloromethane (5.0 mL). To this, triethylamine (278 muL, 2.00 mmol) and methanesulfonyl chloride (116 muL, 1.50 mmol) were added, and the mixture was stirred overnight. After a saturated aqueous solution of sodium hydrogen carbonate was added to the reaction mixture, extraction with chloroform was performed twice. The organic layer was dried over anhydrous magnesium sulfate. After filtration and concentration under reduced pressure, the residue was purified by silica gel column chromatography to give Compound A80 (116 mg, yield: 74%). ESI-MS: m/z 158 [M + H]+; 1H NMR (CDCl3)delta(ppm): 3.94 (s, 3H), 4.55 (s, 2H), 6.76 (d, J = 8.4 Hz, 1H), 7.62 (dd, J = 2.4, 8.4 Hz, 1H), 8.15 (d, J = 2.4 Hz, 1H).

Statistics shows that 65873-72-5 is playing an increasingly important role. we look forward to future research findings about 6-Methoxynicotinaldehyde.

Reference:
Patent; Kyowa Hakko Kirin Co., Ltd.; EP2308880; (2011); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem