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CAS No. : | 113443-62-2 | MDL No. : | MFCD00969010 |
Formula : | C13H13NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | YSNHBNFKJLVKGA-UHFFFAOYSA-N |
M.W : | 215.25 | Pubchem ID : | 3850908 |
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: |
* 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 |
---|---|---|
57% | A solution of 3-fiuoro~4~picoline (5-2, 3.2 g, 29 mmol, 2.9 ml.) in THF (200 mL) under nitrogen atmosphere at -78 C was treated with LDA [freshly prepared by treating diisopropylamine (5.3 g, 53 mmol, 7.4 mL) in THF (50 mL) with 2.5 M n-BuLi in hexanes for 30 minutes under nitrogen atmosphere in an ice bath] for 10 minutes. The mixture stirred 60 minutes and was treated with neat ,0-dimeth l-2-napht1iaienehydroxamic acid (5-1, 7.5 g, .35 mmol) dropwise over ten minutes. The mixture stirred an additional two hours then saturated aqueous ammonium chloride (20 mL) was added to the mixture and stirring continued an additional two hours while the temperature of the mixture rose to 20 °C. Approximately 200 mL of solvent was removed from the mixture in vacuo and the residue was diluted with ethyl acetate (200 mL) and washed with water (3 x 100 mL), The product was extracted with IN HO (6 x 75 mL) and the combined acidic extracts were neutralized with solid sodium carbonate to pH 9. The product was extracted with ethyl acetate (2 x 100 mL) and the extracts were dried ( a2S04) and evaporated. The product 5-3 was obtained as a light yellow crystalline solid (4.4 g, 57percent). - MR (300 MHz, CDC13): delta 8.57 (s, 1H), 8.50 (d, J - 1.5 Hz, IH), 8.41 ( dd. J = 4.6 Hz, J - 1.0 Hz, 1H ), 8.07 (dd, J = 8.2 Hz, J = 1.5 Hz), 8.01 (d, J = 18.7 Hz, IH), 7.94 (m, 2H), 7.68-7.57 (m, 3H), 4.52 (s, 2H); ESI MS (M + H)+ - 266; HPLC method A = 4.29 minutes. |