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2-Chloropyridine-5-acetic acid ethyl ester

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2-Chloropyridine-5-acetic acid ethyl ester Basic information
Product Name:2-Chloropyridine-5-acetic acid ethyl ester
Synonyms:Ethyl 2-(6-chloropyridin-3-yl)acetate;ETHYL (6-CHLOROPYRIDIN-3-YL)-ACETATE;6-Chloro-3-pyridineacetic acid ethyl ester;3-Pyridineacetic acid, 6-chloro-, ethyl ester;Ethyl 6-Chloropyridine-3-acetate;2-CHLOROPYRIDINE-5-ACETIC ACID ETHYL ESTER ISO 9001:2015 REACH;Ethyl 2-Chloropyridine-5-acetate;2-CHLOROPYRIDINE-5-ACETIC ACID ETHYL
CAS:197376-47-9
MF:C9H10ClNO2
MW:199.63
EINECS:
Product Categories:pyridine series;Pyridine;Pyridines
Mol File:197376-47-9.mol
2-Chloropyridine-5-acetic acid ethyl ester Structure
2-Chloropyridine-5-acetic acid ethyl ester Chemical Properties
Boiling point 285.8±25.0 °C(Predicted)
density 1.217±0.06 g/cm3(Predicted)
storage temp. under inert gas (nitrogen or Argon) at 2-8°C
pka-0.34±0.10(Predicted)
AppearanceColorless to light yellow Liquid
InChIInChI=1S/C9H10ClNO2/c1-2-13-9(12)5-7-3-4-8(10)11-6-7/h3-4,6H,2,5H2,1H3
InChIKeyHNMKCAOYIPYXRD-UHFFFAOYSA-N
SMILESC1=NC(Cl)=CC=C1CC(OCC)=O
Safety Information
MSDS Information
2-Chloropyridine-5-acetic acid ethyl ester Usage And Synthesis
Synthesis
Ethanol

64-17-5

2-(6-Chloropyridin-3-yl)acetic acid

39891-13-9

2-CHLOROPYRIDINE-5-ACETIC ACID ETHYL ESTER

197376-47-9

The general procedure for the synthesis of ethyl 2-(6-chloropyridin-3-yl)acetate from ethanol and 2-chloropyridine-5-acetic acid was as follows: to an ethanolic solution of 6-chloro-3-pyridineacetic acid (1 g, 5.83 mmol) was slowly added concentrated sulfuric acid (1.6 mL). The reaction mixture was heated to reflux and kept for 4 hours. Upon completion of the reaction, the mixture was cooled to room temperature and concentrated in a rotary evaporator to remove most of the ethanol. The concentrated residue was dissolved in ethyl acetate and subsequently washed with saturated sodium bicarbonate solution to neutralize the residual acid. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the crude product. Finally, the crude product was purified by silica gel column chromatography to afford ethyl 2-(6-chloropyridin-3-yl)acetate (1.1 g, 95% yield).

References[1] Patent: WO2013/13817, 2013, A1. Location in patent: Page/Page column 99
[2] Patent: WO2013/13815, 2013, A1. Location in patent: Page/Page column 147
[3] Patent: US2013/29961, 2013, A1. Location in patent: Paragraph 0664
[4] Patent: US2013/29962, 2013, A1. Location in patent: Paragraph 0815
[5] Chemical Communications, 2015, vol. 51, # 84, p. 15446 - 15449
2-Chloropyridine-5-acetic acid ethyl ester Preparation Products And Raw materials
Raw materials2-Chloro-5-pyridineacetonitrile-->Ethanol-->2-(6-Chloropyridin-3-yl)acetic acid
Tag:2-Chloropyridine-5-acetic acid ethyl ester(197376-47-9) Related Product Information
3-(3-Pyridyl)acrylic acid 6-CYANONICOTINIC ACID 4-(N,N-DIMETHYLAMINO)PHENYLBORONIC ACID, PINACOL ESTER 2-CYANO-3-PYRIDINECARBOXYLIC ACID METHYL ESTER (6-Chloro-pyridin-3-yl)-oxo-acetic acid ethyl ester 2-Chloropyridine-5-acetic acid ethyl ester 4-Ethoxy-5-nitro-α-chloropyridine-2-acetic acid ethyl ester α-Chloro-3-nitro-6-chloropyridine-2-acetic acid ethyl ester ETHYL 3-PYRIDYLACETATE 3-Pyridylacetic acid methyl pyridine-3-acetate 2-CHLOROPYRIDINE-5-ACETIC ACID