ChemicalBook CAS DataBase List 4-Aminopyridine-2-carboxylic acid

4-Aminopyridine-2-carboxylic acid synthesis

6synthesis methods

Product Name:4-Aminopyridine-2-carboxylic acid
CAS Number:100047-36-7
Molecular formula:C6H6N2O2
Molecular Weight:138.12

1918-02-1

100047-36-7

General procedure for the synthesis of 4-aminopyridine-2-carboxylic acid from 4-amino-3,5,6-trichloropyridine-2-carboxylic acid: a thick suspension formed by Picloram (8 g, 33 mmol) and 10% Pd/C (1.2 g) in a 10% aqueous LiOH solution (44 mL) was purged twice with hydrogen, and then under a hydrogen atmosphere (45 PSI) at 40°C for 4 hours with stirring. Subsequently, the mixture was heated to 70°C and maintained for 12 hours. Upon completion of the reaction, the cooled suspension was filtered through diatomaceous earth. The filtrate was acidified to pH=3 in concentrated HCl (~3.5 mL), at which point a precipitate was generated. The solid product was collected by filtration and dried overnight under high vacuum to give the final 4-aminopyridine-2-carboxylic acid as a beige solid (4.6 g, 99% yield).LCMS analysis showed m/z 139.1 (M + H)+ with a retention time of 0.21 minutes.

1918-02-1 Synthesis

1918-02-1
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$14.14/1gm:

100047-36-7
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$18.00/250mg

Yield:100047-36-7 99%

Reaction Conditions:

Stage #1:picloram with hydrogen;lithium hydroxide;palladium 10% on activated carbon in water at 40 - 70; under 2327.23 Torr; for 16 h;
Stage #2: with hydrogenchloride in water; pH=3

Steps:

38.38A
Intermediate 38A 4-aminopicolinic acid A thick suspension of Picloram (8g, 33 mmol) and 10% Pd / C (1.2g) in a 10% LiOH aqueous solution (44 mL) was purged with hydrogen gas twice then stirred under a hydrogen atmosphere (45 PSI) at 40°C for 4 hours. The mixture was then heated to 70°C for 12 hours. The cooled suspension was filtered on Celite. The filtrate was made acidic (pH = 3) with concentrated HCI (app. 3.5 mL) at wich point a precipitate formed. The solid was filtered off and dried under Hi-Vac overnight to afford the title compound as a beige solid (4.6g, 99%). LCMS m/z 139.1 (M + H)⁺, ret. time= 0.21 min.

References:

UNIVERSITÉ DE MONTRÉAL;RUEL, Réjean;CHANTIGNY, Yves;MARINIER, Anne;RENÉ, Patricia;BOUVIER, Michel WO2012/3576, 2012, A1 Location in patent:Page/Page column 96

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