ChemicalBook CAS DataBase List 3-Aminopyridine-2-carboxylic acid methyl ester

3-Aminopyridine-2-carboxylic acid methyl ester synthesis

5synthesis methods

Product Name:3-Aminopyridine-2-carboxylic acid methyl ester
CAS Number:36052-27-4
Molecular formula:C7H8N2O2
Molecular Weight:152.15

To a solution of 3-aminopyridine-2-carboxylic acid (20 g, 144.9 mmol) in methanol (300 mL) was added conc. sulfuric acid (5.4 mL), and the mixture was heated under reflux for 5 days. The reaction mixture was concentrated under reduced pressure, water was added thereto, and sodium carbonate was added thereto until the complete of foaming. The mixture was extracted with dichloromethane (x3), the organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give methyl 3-aminopyridine-2-carboxylate (17.0 g, 77%) as a pale yellow solid. 1H-NMR(300MHz,CDCl3):δ3.95(3H,s),5.72(2H,brs),7.03(1H,dd,J=0.99,8. 35Hz),7.18-7.21(1H,m),8.05(1H,dd,J=0.96,4.04Hz).

67-56-1 Synthesis

67-56-1
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1462-86-8 Synthesis

1462-86-8
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3-Aminopyridine-2-carboxylic acid methyl ester

36052-27-4
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$8.00/250mg

Yield: 77%

Reaction Conditions:

with sulfuric acid for 120 h;Reflux;

Steps:

135.1 (Step 1)
(Step 1) (1070) To a solution of 3-aminopyridine-2-carboxylic acid (20 g, 144.9 mmol) in methanol (300 mL) was added conc. sulfuric acid (5.4 mL), and the mixture was heated under reflux for 5 days. The reaction mixture was concentrated under reduced pressure, water was added thereto, and sodium carbonate was added thereto until the complete of foaming. The mixture was extracted with dichloromethane (x3), the organic layer was dried over sodium sulfate, and the solvent was evaporated under reduced pressure to give methyl 3-aminopyridine-2-carboxylate (17.0 g, 77%) as a pale yellow solid. ¹H-NMR(300MHz,CDCl₃):δ3.95(3H,s),5.72(2H,brs),7.03(1H,dd,J=0.99,8. 35Hz),7.18-7.21(1H,m),8.05(1H,dd,J=0.96,4.04Hz).

References:

Takeda Pharmaceutical Company Limited;YAMAMOTO, Satoshi;SHIRAI, Junya;FUKASE, Yoshiyuki;SATO, Ayumu;KOUNO, Mitsunori;TOMATA, Yoshihide;OCHIDA, Atsuko;YONEMORI, Kazuko;ODA, Tsuneo;IMADA, Takashi;YUKAWA, Tomoya EP2975031, 2016, A1 Location in patent:Paragraph 1070

1462-86-8 Synthesis

1462-86-8
258 suppliers
$10.00/1g