ChemicalBook CAS DataBase List Ethyl 6-aminopicolinate

Ethyl 6-aminopicolinate synthesis

8synthesis methods

Product Name:Ethyl 6-aminopicolinate
CAS Number:69142-64-9
Molecular formula:C8H10N2O2
Molecular Weight:166.18

23628-31-1

64-17-5

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).

23628-31-1 Synthesis

23628-31-1
252 suppliers
$6.00/1g

64-17-5 Synthesis

64-17-5
814 suppliers
$10.00/50g

69142-64-9
88 suppliers
$8.00/100mg

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

23628-31-1 Synthesis

23628-31-1
252 suppliers
$6.00/1g

69142-64-9
88 suppliers
$8.00/100mg

References