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ChemicalBook CAS DataBase List Ethyl 6-aminopicolinate
69142-64-9

Ethyl 6-aminopicolinate synthesis

8synthesis methods
6-Aminopyridine-2-carboxylic acid

23628-31-1

Ethanol

64-17-5

Ethyl 6-aminopicolinate

69142-64-9

6-Amino-2-pyridinecarboxylic acid (6.0 g, 43.5 mmol) was dissolved in ethanol (150 mL) at 0 °C and sulfoxide chloride (12.0 g, 101 mmol) was added slowly. The reaction mixture was heated to reflux with continuous stirring for 12 hours. Upon completion of the reaction, it was cooled to room temperature and the reaction mixture was subsequently concentrated under reduced pressure. The pH was adjusted to 9 with saturated aqueous sodium carbonate solution and concentrated again under reduced pressure. Dichloromethane (150 mL) was added to the residue, stirred vigorously for 30 minutes at room temperature and filtered. The filtrate was concentrated under reduced pressure to give ethyl 6-aminopyridine-2-carboxylate (5.5 g, 76% yield).

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Yield: 76%

Reaction Conditions:

Stage #1:6-aminopicolinic acid;ethanol with thionyl chloride at 0;Reflux;
Stage #2: with sodium carbonate in water; pH=9

Steps:

26.1
To a solution of 2-amino-6-pyridinecarboxylic acid (90; 6.0 g, 43.5 mmol) in ethanol (150 mL) was added SOCl2 (12.0 g, 101 mmol) at 0 0C. The resulting reaction mixture was stirred under reflux for 12 h. Upon cooling to room temperature, the reaction mixture was concentrated under reduced pressure. Enough saturated aqueous Na2CO3 solution was added to adjust the pH = 9. The mixture was concentrated under reduced pressure and dichloromethane (150 mL) was added to the resulting residue. The mixture was stirred vigorously at room temperature for 30 min and then filtered. The filtrate was concentrated under reduced pressure to afford ethyl 6-aminopicolinate 91 (5.5 g, 76%).

References:

SIRTRIS PHARMACEUTICALS, INC.;VU, Chi, B.;DISCH, Jeremy, S.;NG, Pui, Yee;BLUM, Charles, A.;PERNI, Robert, B. WO2010/3048, 2010, A1 Location in patent:Page/Page column 107

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