Category: 63874-99-7

Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 63874-99-7, name is 1-(4-Chlorophenyl)-1H-pyrazole-4-carbaldehyde, A new synthetic method of this compound is introduced below., Recommanded Product: 63874-99-7

General procedure: 5 mmol 1-Arylpyrazole-4-carbaldehyde, 5 mmol 2-methyl-8-hydroxyl quinoline and 20 mL acetic anhydride were stirred and sealed in a Teflon-lined stainless steel autoclave (25 mL), kept at 160 C for 4 days and then cooled to room temperature. Resultant mixed solution was poured into 100 mL H2O, followed by extractionwith CH2Cl2 (3 50 mL) and rotary evaporation to remove solvent. As-separated crystalline precipitates were dissolved in 25 mL DMF, followed by dropwise addition of 20 mL of aqueous HCl (volume fraction: 36%) at 80 C in a reaction period of 5 h. Then the reactants were allowed to react for additional 4 h after 25 mL of triethylamine was added dropwise. Upon completion of the reaction, the hot mixture was poured into ice water (250 mL) and stirred overnight, followed by extraction with CH2Cl2 (4 100 mL).The combined organic layers were washed with saturated NaCl solution and dried with anhydrous Na2SO4. Crude mixed products were obtained after residual solvent was evaporated under reduced pressure, and as-obtained crude products were purified by column chromatography (silica gel, ethyl acetate/petroleum ether).

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Article; Ren, Tiegang; Wang, Jie; Li, Guihui; Cheng, Hongbin; Li, Yongzhe; Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy; vol. 129; (2014); p. 7 – 13;,
Pyrazole – Wikipedia,
Pyrazoles – an overview | ScienceDirect Topics

Application of 63874-99-7,Some common heterocyclic compound, 63874-99-7, name is 1-(4-Chlorophenyl)-1H-pyrazole-4-carbaldehyde, molecular formula is C10H7ClN2O, 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.

Step 3: A stirring solution of compound 17 (8.0 g, 38.8 mmol) in acetone (100 mL) was cooled to 0 C. Jones reagent (50 mL) was added drop wise to this reaction mixture and mixture was stirred for 1 h at room temperature. After completion of the reaction (monitored by TLC), excess Jones reagent was quenched with the addition of isopropanol. Solid formed in the reaction was filtered off and filtrate was extracted with diethyl ether (2*400 mL). The organic layer was then separated, dried over sodium sulphate and concentrated in vacuo to give crude mass which was purified by giving washings of 10% ethyl acetate in hexanes (100 mL) to afford 1-(4-chloro-phenyl)-1H-pyrazole-4-carboxylic acid 18 as an off white solid (6. g, 27 mmol, 70% yield). 1H NMR (400 MHz, DMSO): delta=12.69 (br, 1H), 9.06 (s, 1H), 8.10 (s, 1H), 7.97-7.94 (d, 2H), 7.60-7.57 (d, 2H); low resolution mass spectrum (ES+) m/z 222.9 ([M+H)+]; calcd for C10H7ClN2O2+H 223.0].

The synthetic route of 63874-99-7 has been constantly updated, and we look forward to future research findings.

Synthetic Route of 63874-99-7, These common heterocyclic compound, 63874-99-7, name is 1-(4-Chlorophenyl)-1H-pyrazole-4-carbaldehyde, 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.

The typical procedure to produce it is as follows: in a 50 mL round-bottom flask, 5 mmol of 1-(4-chlorophenyl)-1H-pyrazole-4-carbaldehyde, named as compound (1), were added to a stirred solution of ammonium acetate 1.25 mmol in dry nitromethane 25 mL. The reaction mixture was refluxed for 12 h, then was allowed to cool and was poured into water. The precipitate was filtrated to vacuum, dried and the crude product was purified by chromatography on silica, using 50:50 n-hexane-CH2Cl2 as mobile phase. The compound (2) was obtained in 72% of yield, as a yellow solid, with a melting point of 146 C and retardation factor Rf = 0.92 (n-hexane/ethyl acetate 7:3). The main infrared bands and NMR data obtained are briefly summarized as follows: IRmax (KBr) cm-1: 3139 (CAH), 1552 and 1325 (NO2), 970 (C(at)C trans); 1H NMR (500.13 MHz) CDCl3 ():8.17 (1H, s, H-5), 8.00 (1H, d, J = 13.5 Hz, H-b), 7.96 (1H, s, H-3), 7.65 (2H, d, J = 8.9 Hz, H-20 and 60), 7.52 (1H, d, J = 13.5 Hz, H-a), 7.47 (2H, d, J = 8.9 Hz, H-30 and 50); 13C NMR (125.76 MHz) CDCl3 (): 140.7 (C-3), 137.3 (C-10), 135.9 (Ca), 133.3 (C-40), 129.8 (2 C-30 and 50), 129.2 (C-b), 128.3 (C-5), 120.4 (2 C- 20 and 60), 115.4 (C-4).

The synthetic route of 63874-99-7 has been constantly updated, and we look forward to future research findings.