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CAS No. : | 6283-81-4 | MDL No. : | MFCD00160418 |
Formula : | C10H11NO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | APQGYFNHIWMRIJ-UHFFFAOYSA-N |
M.W : | 193.20 | Pubchem ID : | 222197 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
52% | With sodium ethanolate; for 16h;Heating / reflux; | (1). Sodium (38 g, 1.65 mol) was slowly added to 900 mL of ethanol and left to stir at RT for 4 h. Solvent was removed in vacuo. Ethyl acetate (200 mL) was addded to the sodium ethoxide followed by ethyl nicotinate (22.6 mL, 0.166 mol) in 150 mL of ethyl acetate. The reaction was heated to reflux for 16 h. Water (200 mL) was added to the reaction mixture. The aqueous layer was acidified to pH 6 with HCl and extracted with ether. Solvent was removed in vacuo to give a brown oil which was purified by column chromatography (2:1, hexanes-EtOAc), to give 1 (101 g, 52%). |
37.1% | With lithium tert-butoxide; for 4h;Reflux; | Add 10 ml of ethyl acetate to a 25 ml round bottom flask.Ethyl nicotinate 1.0g,Lithium tert-butoxide 0.794g,The reaction was refluxed for 4 hours, and the reaction was completed by TLC. The reaction mixture was cooled to room temperature, and 60 ml of 3M HCl solution was added thereto and stirred for 5 minutes. Then, the organic layer was separated and the aqueous layer was extracted with ethyl acetate (90 ml). Dry over sodium sulfate, filter, concentrate,The compound 3-oxo-(3-pyridyl)propionic acid ethyl ester is obtained.The colorless oil was 0.474 g, and the yield was 37.1%. |
3 g | With sodium ethanolate; for 20h;Reflux; | Ethyl 3-picolinate (2.5 g, 16 mmol) was weighed out in a 250 mL eggplant flask,Followed by 60 mL of EA,NaOEt 12 g (176 mmol),Heated to reflux after 20h to stop the reaction,Was removed by rotary evaporation EA, with 2mol / L HCl adjusted to pH 8-9, 3 times (3 × 40mL), the combined organic phase was extracted with EA, dried over anhydrous Na2SO4, separation and purification by column chromatography (petroleum ether / ethyl acetate = 3/ 1) to give 3 g of a yellow oily liquid which was used directly in the next step. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
11.5 g | Condensation reaction: HPLC detection of 99.85% of ethyl nicotinate, the reaction is over, and the temperature is lowered to 0 C.Then add 66g of ethyl acetate, add 0.04g of TiO2 and sodium ethoxide 8.16g, and heat to reflux at 76 C for 5h; Hydrolysis, refining: reduce the temperature to 0 C, add 50 ml of water, add 100 g of concentrated hydrochloric acid, and then heat to reflux for 5 h.Cool to room temperature, add sodium carbonate solution to adjust pH = 9, extract with chloroform, dry chloroform layer,100-110 C fraction (-0.095 MPa) collected by vacuum distillation 11.5 g of 3-acetylpyridine was obtained in an amount of 99.0%, and the molar yield was 95%. |