6-Chloro-4-methoxynicotinic acid Chemical Properties

Boiling point:

350.7±37.0 °C(Predicted)

Density 

1.430

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

3.13±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C7H6ClNO3/c1-12-5-2-6(8)9-3-4(5)7(10)11/h2-3H,1H3,(H,10,11)

InChIKey

DFXUFJAAXAJWSA-UHFFFAOYSA-N

SMILES

C1=NC(Cl)=CC(OC)=C1C(O)=O

Safety Information

Safety Statements 

24/25

HazardClass 

IRRITANT

HS Code 

29339900

6-Chloro-4-methoxynicotinic acid Usage And Synthesis

Uses

6-Chloro-4-methoxynicotinic acid is used for preparation of benzimidazolylazabicyclooctylethylpiperidines as Ccr5 antagonists for the treatment of HIV infection.

Synthesis

General procedure for the synthesis of 6-chloro-4-methoxynicotinic acid from methyl 6-chloro-4-methoxynicotinate: lithium hydroxide (1.84 g, 43.9 mmol) was added to a solution of the intermediate from step 2 (2.94 g, 14.6 mmol) in a mixture of methanol (30 mL), tetrahydrofuran (30 mL) and water (3 mL) at 0°C. The reaction mixture was stirred at room temperature for 3 hours. The volatiles were removed under reduced pressure and the residue was diluted with water and washed with dichloromethane. The aqueous layer was acidified to pH ≈ 3 with sodium bisulfate solution and extracted with dichloromethane. The combined organic layers were dried and the volatiles were removed under reduced pressure to give the target product 6-chloro-4-methoxynicotinic acid (2.7 g, 98% yield).

References

[1] Patent: US2015/166505, 2015, A1. Location in patent: Paragraph 0342; 0349; 0350
[2] Patent: WO2012/110860, 2012, A1. Location in patent: Page/Page column 99

6-Chloro-4-methoxynicotinic acid(716362-10-6)Related Product Information

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• 4-Methoxyphenylacetone
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• 6-CHLORO-4-ETHOXYNICOTINIC ACID
• Methyl chloroformate