METHYL 2-CHLORO-5-IODONICOTINATE Chemical Properties

Melting point:

70-73°

storage temp. 

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

solubility 

Chloroform (Slightly), Methanol (Slightly)

form 

Solid

color 

White

Safety Information

HazardClass 

IRRITANT

HS Code 

2933399990

METHYL 2-CHLORO-5-IODONICOTINATE Usage And Synthesis

Synthesis

Step 2 of Scheme 13: Methyl 5-iodo-2-hydroxynicotinate (4.75 g, 17.1 mmol) was dissolved in trichlorophosphorus (50 mL) and heated to reflux for 24 hours. After completion of the reaction, the solvent was removed by rotary evaporator. The crude product was neutralized with saturated sodium bicarbonate solution and subsequently extracted with ether. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated by rotary evaporator. The crude product was purified by silica gel column chromatography to afford 4.3 g (85% yield) of methyl 2-chloro-5-iodonicotinate using a hexane solution of 5% ethyl acetate as eluent. The physical and chemical properties of this compound have been documented in Journal of Organic Chemistry, 1989, vol. 54.

References

[1] Patent: US2005/203081, 2005, A1. Location in patent: Page/Page column 13; 33
[2] Journal of Medicinal Chemistry, 1993, vol. 36, # 18, p. 2676 - 2688
[3] Patent: US5250548, 1993, A
[4] Patent: WO2008/76425, 2008, A1. Location in patent: Page/Page column 54
[5] Patent: WO2008/130600, 2008, A2. Location in patent: Page/Page column 46

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