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With hydrazine In ethanol; water at 70℃; for 12 h;
A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 70° C. for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51percent yield; 1H NMR: (DMSOd6) 1.04 (t, 3H), 2.41 (q, 2H), 4.4 (br s, 2H).
25%
Stage #1: for 0.0833333 h; Stage #2: at 40℃; for 12 h; Stage #3: With hydrogenchloride In water at 50℃; for 2 h;
Example 295a 5-Ethylisoxazol-3-amine 295a To a solution of 3-oxopentanenitrile (1.0 g, 10.3 mmol) in water (20 mL) was added NaOH (535.6 mg, 13.4 mmol). After stirring for 5 minutes, hydroxylamine hydrochloride (787.4 mg, 11.33 mmol) was added and mixture was heated at 40 °C for 12 h. At this point, conc. HCl (3 mL) was added and the reaction mixture was heated at 50 °C for 2 h. Analysis of the reaction mixture by LCMS showed complete conversion to the desired product. It was then cooled to room temperature and adjusted the pH to 10 with aqueous NaOH (30percent). The mixture was extracted with ethyl acetate (3 X 50 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 2:1 petroleum ether/ethyl acetate to afford 295a as a yellow solid (300 mg, 25percent). MS-ESI: [M+H]+ 113.3. 1H NMR (500 MHz, DMSO-d6) 5.55 (s, 1H), 5.40 (s, 2H), 2.56-2.52 (m, 2H), 1.13 (t, J= 7.5 Hz, 3H).
With hydrazine; In ethanol; water; at 70℃; for 12h;
A mixture of a portion (0.6 g) of the material so obtained, hydrazine hydrate (0.28 ml) and ethanol (45 ml) was heated at 70 C. for 12 hours. The solvent was evaporated and the residue was purified by column chromatography on silica using a 19:1 mixture of methylene chloride and methanol as eluent. There was thus obtained the required starting material in 51% yield; 1H NMR: (DMSOd6) 1.04 (t, 3H), 2.41 (q, 2H), 4.4 (br s, 2H).
25%
Example 295a 5-Ethylisoxazol-3-amine 295a To a solution of <strong>[33279-01-5]3-oxopentanenitrile</strong> (1.0 g, 10.3 mmol) in water (20 mL) was added NaOH (535.6 mg, 13.4 mmol). After stirring for 5 minutes, hydroxylamine hydrochloride (787.4 mg, 11.33 mmol) was added and mixture was heated at 40 C for 12 h. At this point, conc. HCl (3 mL) was added and the reaction mixture was heated at 50 C for 2 h. Analysis of the reaction mixture by LCMS showed complete conversion to the desired product. It was then cooled to room temperature and adjusted the pH to 10 with aqueous NaOH (30%). The mixture was extracted with ethyl acetate (3 X 50 mL). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was purified by silica-gel column chromatography eluting with 2:1 petroleum ether/ethyl acetate to afford 295a as a yellow solid (300 mg, 25%). MS-ESI: [M+H]+ 113.3. 1H NMR (500 MHz, DMSO-d6) 5.55 (s, 1H), 5.40 (s, 2H), 2.56-2.52 (m, 2H), 1.13 (t, J= 7.5 Hz, 3H).
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