4-Amino-3-pyridinecarboxylic acid Chemical Properties

Melting point:

307-312 °C

Boiling point:

253.51°C (rough estimate)

Density 

1.3471 (rough estimate)

refractive index 

1.5100 (estimate)

storage temp. 

Keep in dark place,Inert atmosphere,Room temperature

solubility 

Soluble in aqueous acid and base.

pka

2.94±0.10(Predicted)

form 

Powder

color 

Cream to yellow

InChI

InChI=1S/C6H6N2O2/c7-5-1-2-8-3-4(5)6(9)10/h1-3H,(H2,7,8)(H,9,10)

InChIKey

IASBMUIXBJNMDW-UHFFFAOYSA-N

SMILES

C1=NC=CC(N)=C1C(O)=O

CAS DataBase Reference

7418-65-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

TSCA 

N

HazardClass 

IRRITANT

HS Code 

29333990

MSDS

• Language:English Provider:ACROS
• Language:English Provider:ALFA

4-Amino-3-pyridinecarboxylic acid Usage And Synthesis

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

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