Synthetic Route of 17635-45-9, These common heterocyclic compound, 17635-45-9, name is 4-Pyrazol-1-yl-phenylamine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Example 11 4-Pyridinecarboxyaldehyde 4-(pyrazol-1-yl)phenylhydrazone; [Show Image] 4-(Pyrazol-1-yl)phenylamine (646 mg) was dissolved in water (10 ml) and concentrated hydrochloric acid (10 ml), and an aqueous solution (4 ml) of sodium nitrite (336 mg) was added to the solution at 0°C over 30 minutes. After stirring at the same temperature for 30 minutes, a concentrated hydrochloric acid solution (3 ml) of tin chloride dihydrate (1.83 g) was added to the mixture, followed by stirring at room temperature for 30 minutes. The reaction mixture was alkalified by adding 20percent aqueous solution of potassium hydroxide and extracted with chloroform: methanol = 9:1 (100 ml) twice. After drying over anhydrous sodium sulfate, the solvent was evaporated to obtain a reddish brown residue. The residue and 4-pyridinecarboxyaldehyde (324 mul) were dissolved in ethanol (8 ml) and heated under reflux for 15 hours. The solvent was evaporated, and then the residue was purified by flash silica gel column chromatography (chloroform: methanol = 10:1) to obtain the title compound (107 mg) as a reddish brown solid. 1H-NMR (400 MHz, D2O) delta: 6.35 (1H, s), 6.95 (2H, d, J=8.6 Hz), 7.14 (1H, s), 7.22 (2H, d, J=9.0 Hz), 7.47 (2H, d, J=5.8 Hz), 7.51 (1H, s), 7.76 (1H, s), 8.07 (2H, d, J=5.8 Hz). ESI-MS m/z: 264 (M+H)+
Statistics shows that 4-Pyrazol-1-yl-phenylamine is playing an increasingly important role. we look forward to future research findings about 17635-45-9.
Reference:
Patent; DAIICHI PHARMACEUTICAL CO., LTD.; EP1612204; (2006); A1;,
Pyrazole – Wikipedia,
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