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CAS No. : | 26510-52-1 | MDL No. : | MFCD00094022 |
Formula : | C10H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | FQHXWZMJALFSJJ-UHFFFAOYSA-N |
M.W : | 193.20 | Pubchem ID : | 2736461 |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In pyridine; at 20℃; for 16h; | Ethyl picolinoylacetate (4.7 g, 24.3 mmol) and the product of Preparation 1 (5.0 g, 36.5 mmol) are mixed in 10 ML of pyridine. The reaction mixture is stirred overnight at RT and then evaporated to a solid mass. The crude mixture is purified by MPLC on silica gel (40% EtOAc/Hexanes) to give the title compound, 6.63 g (95%), as a liquid. MS ES+ m/e 276. 1 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | With pyridine; at 20℃; for 20h; | B. Preparation of 3-(2-Oxo-pyrrolidin-l-ylimino)-3-(pyridin-2-yl)-propionic acid ethyl ester; Place l-aminopyrrolidin-2-one hydrochloride (Zubek, A. Z. Chem., 1969, 9(2), 58; 155.6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-oxo-3-pyridin-2-yl-propionic acid ethyl ester (Preparation 2, Part A; 200 g, 1.04 mol) and pyridine (400 mL). Stir the reaction mixture at room temperature for 20 h.Dilute the mixture with water (500 mL) and extract with toluene (2 x 500 mL). Combine EPO <DP n="19"/>the organic layers, dry (sodium sulfate), filter, and concentrate in vacuo to yield 280 g (98%) of the subtitled compound as a dark oil. MS (ES) m/z = 276 (M+H). |
98% | With pyridine; at 20℃; for 20h; | Place L-AMINOPYRROLIDIN-2-ONE hydrochloride (Zubek, A. Z. CHEM., 1969, 9 (2), 58; 155.6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-oxo-3-pyridin-2-yl-propionic acid ethyl ester (200 g, 1.04 mol) then pyridine (400 mL). Stir the reaction mixture at room temperature for 20 h. Dilute the mixture with water (500 mL), and-extract with toluene (2 x 500 mL). Combine the organic layers, dry (sodium sulfate), filter and concentrate in vacuo to yield the subtitled compound as a dark oil (280 g, 98%). MS ES+ M/E 276 (M+1). |
98% | In pyridine; at 20℃; for 20h; | Place l-aminopyrrolidin-2-one hydrochloride (Zubek, A. Z. Chem., 1969, 9 (2), 58 ; 155. 6 g, 1.14 mol) in a 3 L flask equipped with mechanical stirrer and nitrogen inlet. Add 3-oxo-3-pyridin-2-yl-propionic acid ethyl ester (Preparation 3-A ; 200 g, 1.04 mol) and pyridine (400 mL). Stir the reaction mixture at room temperature for 20 h. Dilute the mixture with water (500 mL) and extract with toluene (2 x 500 mL). Combine the organic layers, dry (sodium sulfate), filter, and concentrate in vacuo to yield 280 g (98%) of the subtitled compound as a dark oil. MS ES+ m/e 276 (M+1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
40% | With acetic acid; at 115℃; for 12h;Inert atmosphere; | (a) Ethyl 3-oxo-3-(pyridin-2-yl)propanoate (500 mg, 2.6 mmol) was taken in AcOH (50 mL) in a 250 mL round bottom flask under N2. To it was added <strong>[4922-98-9]3-phenyl-1H-1,2,4-triazol-5-amine</strong> (497 mg, 3.1 mmol). The reaction mixture was heated at 115 °C for 12 h. The reaction mixture was then evaporated to dryness using toluene as an azeotropic solvent and triturated with diethyl ether. This was finally dried under high vacuum which afforded 66b as a deep brown solid (300 mg, 40percent). This was then used in the next step without any further purification. LCMS(ESI) m/z 288.02 [M-H+]; 57percent (purity). |
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