These common heterocyclic compound, 54605-72-0, name is 1-Phenylpyrazole-4-carboxaldehyde, 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. Computed Properties of C10H8N2O
A mixture of 1-phenylpyrazole-4-carbaldehyde (18.5 mg, 0.11 mmol), paracyclophanyl piperazine (31.4 mg, 0.11 mmol) and sodium triacetoxyborohydride (27.5 mg, 0.13 mmol) in dichloromethane (1.5 mL) was stirred at room temperature for 24 h. Then, the mixture was added to a saturated aqueous solution of NaHCO3 and extracted with dichloromethane. The organic layer was dried (Na2SO4) and evaporated and the residue was purified by flash chromatography (petroleum ether/ethyl acetate 4:6) to give pure 4 (35.2 mg, 72%) as a colorless solid (mp 78 C). EI-MS: m/z 448 (M+); 1H NMR: (CDCl3, 360 MHz) delta (ppm): 2.60-2.81 (m, 5H), 2.85-3.12 (m, 9H), 3.25 (ddd, J = 12.3 Hz, 9.0 Hz, 6.0 Hz, 1H), 3.37 (ddd, J = 12.7 Hz, 9.7 Hz, 2.4 Hz, 1H), 3.60 (s, 2H), 5.71 (d, J = 1.8 Hz, 1H), 6.27 (dd, J = 7.8 Hz, 1.8 Hz, 1H), 6.35 (dd, J = 7.9 Hz, 1.9 Hz, 1H), 6.40 (d, J = 7.8 Hz, 1H), 6.44 (dd, J = 7.9 Hz, 1.9 Hz, 1H), 6.52 (dd, J = 7.9 Hz, 1.9 Hz, 1H), 6.69 (dd, J = 7.9 Hz, 1.9 Hz, 1H), 7.24-7.31 (m, 1H), 7.41-7.48 (m, 2H), 7.67-7.73 (m, 3H), 7.92 (s, 1H); IR: (KBr) nu (cm-1): 1596. Anal. Calcd for C30H32N4: C, 80.32; H, 7.19; N, 12.49. Found: C, 80.63; H, 7.13; N, 12.32.
The synthetic route of 1-Phenylpyrazole-4-carboxaldehyde has been constantly updated, and we look forward to future research findings.
Reference:
Article; Sanna, Fabrizio; Ortner, Birgit; Huebner, Harald; Loeber, Stefan; Tschammer, Nuska; Gmeiner, Peter; Bioorganic and Medicinal Chemistry; vol. 21; 7; (2013); p. 1680 – 1684;,
Pyrazole – Wikipedia,
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