3-CHLOROISONICOTINIC ACID ETHYL ESTER synthesis
- Product Name:3-CHLOROISONICOTINIC ACID ETHYL ESTER
- CAS Number:211678-96-5
- Molecular formula:C8H8ClNO2
- Molecular Weight:185.61
64-17-5
211678-96-5
General procedure for the synthesis of ethyl 3-chloroisonicotinate from ethanol: 3-chloroisonicotinate (1.0 g, 6.35 mmol) was suspended in thionyl chloride (10 ml) and heated to reflux for 2.5 hours. Upon completion of the reaction, the solution was cooled to room temperature, concentrated to dryness and subsequently azeotropized with toluene (10 ml) to give an oil. The resulting oily substance was slowly added dropwise to a cooled mixture of ethanol (15 ml) and diisopropylethylamine (DIPEA) at 0°C, the dropwise process was controlled to be completed within 10 minutes. The reaction mixture was stirred at room temperature for 18 hours. At the end of the reaction, the reaction solution was concentrated in vacuum, diluted with water (20 ml) and extracted with ethyl acetate (30 ml). The organic phase was dried over anhydrous sodium sulfate and concentrated to give ethyl 3-chloroisonicotinate as an orange oil (1.1 g, 94% yield). The product was characterized by 1H NMR (CDCl3, 400MHz): δ 8.72 (s, 1H), 8.59 (d, J = 4.9Hz, 1H), 7.63 (dd, J = 4.9Hz, 0.5Hz, 1H), 4.44 (q, J = 7.3Hz, 2H), 1.42 (t, J = 7.3Hz, 3H).
64-17-5
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211678-96-5
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Yield:211678-96-5 94%
Reaction Conditions:
Stage #1: 3-chloro-isonicotinic acidwith thionyl chloride for 2.5 h;Heating / reflux;
Stage #2: ethanolwith N-ethyl-N,N-diisopropylamine at 0 - 20; for 18.17 h;
Steps:
7
3-Chloro-isonicotinic acid ethyl esterCl O( so N. y[00263] A suspension of 3-chloro-isonicotinic acid (1.0 g, 6.35 mmol) in thionyl chloride (10 ml) was heated under reflux for 2.5 hours. After cooling to ambient temperature, the solution was concentrated to dryness and then azeotroped with toluene (10 ml) to afford an oil. The resultant oil was added dropwise over 10 minutes to a cooled (O0C) solution of ethanol (15 ml) and DIPEA (5 ml). The reaction was stirred at room temperature for 18 hours then concentrated in vacuo before water (20 ml) was added. The solution was extracted with ethyl acetate (30 ml) and the organic phase was dried over sodium sulfate then concentrated to give the title compound as an orange oil (1.1 g, 94%). IH NMR (CDCl3, 400MHz) 8.72 (s, IH), 8.59 (d, J = 4.9 Hz, IH), 7.63 (dd, J = 4.9 Hz,
References:
WO2008/24724,2008,A1 Location in patent:Page/Page column 68-69
64-17-5
814 suppliers
$10.00/50g
88912-27-0
192 suppliers
$14.00/1g
211678-96-5
62 suppliers
$20.00/1g
88912-27-0
192 suppliers
$14.00/1g
211678-96-5
62 suppliers
$20.00/1g