METHYL 2-CHLORO-6-METHOXYNICOTINATE Chemical Properties

Melting point:

67-69°

Boiling point:

276.8±35.0 °C(Predicted)

Density 

1.288±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

pka

-1.13±0.10(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C8H8ClNO3/c1-12-6-4-3-5(7(9)10-6)8(11)13-2/h3-4H,1-2H3

InChIKey

WDMMBHZPESWUCL-UHFFFAOYSA-N

SMILES

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

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

METHYL 2-CHLORO-6-METHOXYNICOTINATE Usage And Synthesis

Uses

Methyl 2-Chloro-6-methoxynicotinate is used in preparation of Aryl-aniline and Heteroaryl-Aniline compounds useful in topical formulations for treatment of skin diseases.

Synthesis Reference(s)

Journal of Medicinal Chemistry, 46, p. 702, 2003 DOI: 10.1021/jm020270n

Synthesis

General Steps: 1. 2-Chloro-6-hydroxynicotinic acid (3.00 g, 17.3 mmol) and chloroform (30 mL) were added to a 50 mL round-bottomed flask and stirred until completely dissolved. 2. Silver carbonate (11.0 g, 39.8 mmol) and methyl iodide (3.77 mL, 60.5 mmol) were added sequentially to the above solution. 3. The reaction mixture was stirred at 50 °C for 3 hours and the reaction was monitored by TLC. 4. 4. After completion of the reaction, the mixture was vacuum filtered and the filter cake was washed with chloroform. 5. The filtrate and washings were combined and concentrated under reduced pressure in a rotary evaporator to give the crude product. 6. The crude product was purified by fast column chromatography (eluent: 0-100% ethyl acetate/heptane gradient elution) and the target fraction was collected. 7. The target fraction was concentrated under pressure to afford methyl 2-chloro-6-methoxypyridine-3-carboxylate (2.42 g, 69% yield) as a white powder. 8. The product was purified by LCMS (0-100% ethyl acetate/heptane gradient elution). 8. The product was characterized by LCMS (Method D): retention time 1.13 min, m/z = 202 (M + 1).

References

[1] Patent: WO2017/147102, 2017, A1. Location in patent: Paragraph 00376-00377

METHYL 2-CHLORO-6-METHOXYNICOTINATE(95652-77-0)Related Product Information

• Tetramethylsilane
• Mercury
• 2-CHLORO-6-METHOXYNICOTINALDEHYDE
• METHYL 2-CHLORO-6-METHOXYNICOTINATE
• 2-CHLORO-6-METHOXYNICOTINIC ACID
• 2-Chloro-6-hydroxynicotinic acid