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Ethyl 2,6-dichloroisonicotinate

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Ethyl 2,6-dichloroisonicotinate manufacturers

Ethyl 2,6-dichloroisonicotinate Basic information
Product Name:Ethyl 2,6-dichloroisonicotinate
Synonyms:Ethyl 2,6-dichloroisonicotinate;Ethyl 2,6-dichloropyridine-4-carboxylate;2,6-Dichloroisonicotinic acid ethyl ester;2,6-Dichloropyridine-4-carboxylic acid ethyl ester;2,6-dichloroisonicotin ethyl ester;4-Pyridinecarboxylic acid, 2,6-dichloro-, ethyl ester;4-Pyridinecarboxylic acid, 2,6-dichloro-, ethyl ester (9CI, ACI)
CAS:1604-14-4
MF:C8H7Cl2NO2
MW:220.05
EINECS:
Product Categories:Pyridines
Mol File:1604-14-4.mol
Ethyl 2,6-dichloroisonicotinate Structure
Ethyl 2,6-dichloroisonicotinate Chemical Properties
Melting point 67 °C
Boiling point 311.4±37.0 °C(Predicted)
density 1.367±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka-4.27±0.10(Predicted)
AppearanceWhite to yellow Solid
Safety Information
HazardClass IRRITANT
HS Code 2933399990
MSDS Information
Ethyl 2,6-dichloroisonicotinate Usage And Synthesis
Synthesis Reference(s)Journal of Medicinal Chemistry, 45, p. 2484, 2002 DOI: 10.1021/jm0200660
Synthesis
Ethanol

64-17-5

2,6-Dichloroisonicotinic acid

5398-44-7

Ethyl 2,6-dichloroisonicotinate

1604-14-4

To an ice-cold solution of 2,6-dichloroisonicotinic acid (10 g, 52 mmol) in ethanol (100 mL) was slowly added concentrated sulfuric acid (5 mL). The reaction mixture was heated to reflux and held for 12 hours. Upon completion of the reaction, the solvent was evaporated under reduced pressure. The residue was cooled in an ice bath, neutralized to pH neutral with sodium bicarbonate solution and subsequently extracted with ethyl acetate. The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give ethyl 2,6-dichloro-isonicotinate (11 g, 96% yield).

References[1] Patent: WO2017/4609, 2017, A1. Location in patent: Paragraph 0265
[2] Chemistry - A European Journal, 2010, vol. 16, # 9, p. 2830 - 2842
[3] Journal of the Chemical Society, 1897, vol. 71, p. 1082
[4] Journal of the Chemical Society, 1898, vol. 73, p. 441
[5] Journal of Medicinal Chemistry, 1990, vol. 33, # 6, p. 1667 - 1675
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