Description
4-amino Nicotinic acid is a synthetic intermediate that has been used in various syntheses.
Chemical Properties
Light yellow Cryst
Uses
4-Aminonicotinic acid has been used in the preparation of 2-methyl-pyrido-oxazine. It is also used as pharmaceutical intermediate.
Definition
ChEBI: 4-aminonicotinic acid is an aminonicotinic acid in which the amino group is situated at position 4 of the pyridine ring. It has a role as a metabolite. It is an aromatic amine, an aminopyridine and an aminonicotinic acid. It is functionally related to a 4-aminopyridine and a nicotinic acid.
General Description
4-Amino-nicotinic acid is a white to light yellow and faint beige to light beige and faint brown to light brown powder or crystals.
Synthesis
The general procedure for the synthesis of 4-aminopyridine-3-carboxylic acid from 4-aminonicotinic acid methyl ester was as follows: to an aqueous ethanol solution of 4-aminopyridine-3-carboxylic acid methyl ester (2 g, 13.15 mmol) in stirring (120 mL, V/V=1:1) was added LiOH-H2O (1.21 g, 28.80 mmol) at room temperature, and the reaction mixture was subsequently heated to 80°C for 2 h (the progress of the reaction was monitored by TLC to confirm complete consumption of the feedstock). After completion of the reaction, the volatiles were removed under reduced pressure to give the crude product. The crude product was dissolved in water (30 mL) and washed with ethyl acetate (2 x 25 mL) to remove non-polar impurities. The aqueous layer was acidified to pH=1 with 1N HCl solution and subsequently extracted with ethyl acetate (2 x 10 mL). The organic extracts were combined and concentrated under reduced pressure to give a crude residue. The crude product was purified by crystallization from methanol (20 mL) to give finally 4-aminopyridine-3-carboxylic acid (1 g, 55% yield) as an off-white solid.LCMS (ESI+): m/z: 139.31 [M+H]+.
References
[1] Patent: WO2018/125961, 2018, A1. Location in patent: Page/Page column 98; 99; 100
