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In hydrazine hydrate; |
B. 1H-Indazole-5-carbonitrile <strong>[146137-79-3]4-Fluoro-3-formylbenzenecarbonitrile</strong> (4.6 g, 30.85 mmol) was suspended in 20 mL of hydrazine mono-hydrate and the reaction mixture was stirred at room temperature for 48 hours. The title compound was isolated by filtration as a white solid, was washed with small portions of distilled water, and was dried in a vacuum (3.6 g, 81percent yield). The same protocol was used to convert 3.5 g of <strong>[146137-79-3]4-fluoro-3-formylbenzenecarbonitrile</strong> to the title compound and resulted in the isolation of 1.9 g of white solid (80percent yield): 1H NMR (CDCl3) delta 10.45 (br s, 1H), 8.20 (d, 1H), 8.19 (d, 1H), 7.6 (s, 1H); ES-MS 250 [M+1]+. |
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With hydrazine; In water; at 20℃; for 18h; |
2-fluoro-5-cyanobenzaldehyde (1.1 g) is dissolved in hydrazine hydrate (19 ml) and stirred at room temperature for 18 hours. The solution is then distilled and the residue purified by flash column chromatography on silica, eluting with DCM. This gives the title compound (300 mg). |
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With hydrazine hydrate; In N,N-dimethyl-formamide; at 80℃; for 0.416667h;Microwave irradiation; |
A solution of <strong>[146137-79-3]4-fluoro-3-formylbenzonitrile</strong> (1 eq) and hydrazine hydrate (10 eq) in DMF (0.3 M) was heated under microwave irradiation at 80 0C for 25 min.The reaction was partitioned between brine and EtOAc. The organic phase was dried (Na2SO4), filtered and concentrated. Al was obtained by purification through SCX cartridge, eluting with methanol. Volatiles were removed under reduced pressure and the title compound was obtained as a yellow solid.MS (ES) C8H5N3 requires 143, found 144(M+H)+. |
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With hydrazine hydrate; potassium carbonate; In ethanol; at 50℃; for 18h; |
A mixture of <strong>[146137-79-3]4-fluoro-3-formylbenzonitrile</strong> (3.45 g, 23.14 mmol), hydrazine hydrate (32.6 mL, 370 mmol) and potassium carbonate (3.52 g, 25.4 mmol) in ethanol (12 mL) was heated at 50°C overnight (ca. 18 h). The mixture was then cooled and diluted with saturated aqueous ammonium chloride solution (ca. 60 mL) and ethyl acetate (60 mL). The aqueous layer was separated and further extracted with ethyl acetate (5 x 40 mL) and the organics combined, dried over magnesium sulfate, filtered and reduced. The resulting residue was triturated with minimal methanol, ethyl acetate and ether (ca. 15 mL) then filtered. The solid obtained was dried in the vacuum oven to afford the title compound as a pink solid (1.906 g). LCMS (A) m/z: 144 [M+1]+, Rt 0.80 min (acidic). The filtrate was reduced and dried to afford some impure title compound as a reddish pink solid (1.39 g) |
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With potassium carbonate; hydrazine; In ethanol; at 50℃; |
Description 29: 1H-Indazole-5-carbonitrileA mixture of <strong>[146137-79-3]4-fluoro-3-formylbenzonitrile</strong> (3.45 g, 23.14 mmol), hydrazine hydrate (32.6 mL, 370 mmol) and potassium carbonate (3.52 g, 25.4 mmol) in ethanol (12 mL) was heated at 50° C. overnight (ca. 18 h).The mixture was then cooled and diluted with saturated aqueous ammonium chloride solution (ca. 60 mL) and ethyl acetate (60 mL).The aqueous layer was separated and further extracted with ethyl acetate (5*40 mL) and the organics combined, dried over magnesium sulfate, filtered and reduced.The resulting residue was triturated with minimal methanol, ethyl acetate and ether (ca. 15 mL) then filtered.The solid obtained was dried in the vacuum oven to afford the title compound as a pink solid (1.906 g). LCMS (A) m/z: 144 [M+1]+, Rt 0.80 min (acidic).The filtrate was reduced and dried to afford some impure title compound as a reddish pink solid (1.39 g). |
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