ALPHA-[2-(3'-NITROPYRIDINYL)] DIETHYL MALONATE synthesis
- Product Name:ALPHA-[2-(3'-NITROPYRIDINYL)] DIETHYL MALONATE
- CAS Number:64362-41-0
- Molecular formula:C12H14N2O6
- Molecular Weight:282.25
5470-18-8
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105-53-3
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$5.00/25g
64362-41-0
33 suppliers
$306.89/250mg
Yield:64362-41-0 100%
Reaction Conditions:
Stage #1: diethyl malonatewith sodium hydride in dimethyl sulfoxide at 0; for 0.5 h;Inert atmosphere;
Stage #2: 2-Chloro-3-nitropyridine in dimethyl sulfoxide at 100; for 0.25 h;Inert atmosphere;
Steps:
Intermediate 75: Diethyl 2-(3-nitropyridin-2-yl)malonate:
Sodium hydride (60%) (18.22 g, 0.46 mol) was suspended in DMSO (360 ml) under nitrogen atmosphere and cooled to 0°C. Diethyl malonate (69.18 ml, 0.46 mol) was added to the above mixture, warmed to room temperature and stirred for 30 mins. 2-Chloro-3- nitropyridine (31 g, 0.195 mol) was added to the above reaction mixture and heated to 100°C for 15 mins. After 15 mins, Reaction mixture was cooled to 0°C and quenched with aqueous ammonium chloride solution. Aqueous reaction mixture extracted with ethyl acetate (2*250 ml) and ethyl acetate layer washed with water (2*500 ml). Organic layer distilled under vacuum to obtain the titled compound as a brown gel (55.2 g). Yield: 100%. 1H-NMR (δ ppm, DMSO- d6, 400 MHz): 8.88 (dd, J 4.6, 1.3, 1H), 8.61 (dd, J 8.4, 1.4, 1H), 7.75 (dd, J 8.3, 4.7, 1H), 5.59 (s, 1H), 4.20-4.14 (m, 4H), 1.17 (t, J 7.1, 6H).
References:
WO2021/220120,2021,A1 Location in patent:Paragraph 223
5470-18-8
440 suppliers
$6.00/5g
107-83-5
216 suppliers
$10.00/1g
105-53-3
730 suppliers
$5.00/25g
64362-41-0
33 suppliers
$306.89/250mg