2-Chloro-6-hydroxynicotinic acid Chemical Properties

Melting point:

302°C(lit.)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to crystal

color 

White to Light yellow to Light red

InChI

InChI=1S/C6H4ClNO3/c7-5-3(6(10)11)1-2-4(9)8-5/h1-2H,(H,8,9)(H,10,11)

InChIKey

BSCFFOOWFVZSSK-UHFFFAOYSA-N

SMILES

C1(Cl)NC(=O)C=CC=1C(O)=O

CAS DataBase Reference

38025-90-0

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

2-Chloro-6-hydroxynicotinic acid Usage And Synthesis

Uses

2-Chloro-6-hydroxynicotinic acid, as a pharmaceutical intermediate, can be used to prepare N-(2-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridin-3-yl)cyclopropanesulfonamide, which is a MEK inhibitor.

Chemical Properties

Off-white powder

Synthesis

The general procedure for the synthesis of 2-chloro-6-hydroxynicotinic acid from 2,6-dichloronicotinic acid is as follows: 1. 2,6-dichloronicotinic acid (25 g, 130 mmol) and NaOH solution (325 mL, 2N) were added to a 500 mL round bottom flask. 2. The reaction mixture was refluxed at 129°C for 4 hours. 3. Upon completion of the reaction, the mixture was cooled to 0°C. 4. The reaction mixture was acidified to room temperature with 6N aqueous HCl solution. 5. The resulting precipitate was collected by filtration. 6. The precipitate was dried under reduced pressure to give 2-chloro-6-hydroxynicotinic acid (19.87 g, 88% yield).

References

[1] Patent: WO2010/108652, 2010, A1. Location in patent: Page/Page column 97
[2] Patent: WO2008/125820, 2008, A1. Location in patent: Page/Page column 33
[3] Patent: CN108314645, 2018, A. Location in patent: Paragraph 0094; 0095; 0096; 0097

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