ChemicalBook CAS DataBase List 5-NITROISOPHTHALALDEHYDE

5-NITROISOPHTHALALDEHYDE synthesis

6synthesis methods

Product Name:5-NITROISOPHTHALALDEHYDE
CAS Number:36308-36-8
Molecular formula:C8H5NO4
Molecular Weight:179.13

13290-96-5 Synthesis

13290-96-5
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36308-36-8
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Yield:36308-36-8 48%

Reaction Conditions:

with diisobutylaluminium hydride in toluene at -78; for 1 h;Inert atmosphere;

Steps:

Preparation of 2-nitroterephthalaldehyde (S-3)

General procedure: DIBAL-H (1.0 M in toluene, 26.0 mL, 26.0 mmol) was added dropwise to a stirred solution of dimethyl 2-nitroterephthalate (3.0 g, 12.54 mmol) in dry toluene (100 mL) at -78°C under an nitrogen atmosphere. After completing addition, the mixture was stirred continuously for 1 h below -70°C. The resulting mixture was quenched with saturated NaHCO₃ solution (10 mL) and then adjusted PH 6-7 with 10% HCl aqueous solution, extracted with EtOAc (150 mL×2). The combined organic layers were concentrated under reduced pressure. The residue was purified by flash column chromatography (eluent, 5-10% EtOAc in petroleum ether) to afford 2-nitroterephthalaldehyde S-3 (1.62 g, 72%) as a slight yellow crystalline solid.

References:

An, Jing;Fang, Xiong;Huang, Lina S.;Huang, Ziwei;Liang, Boqiang;Meng, Qian;Schooley, Robert T.;Wang, Juan;Xu, Yan;Zhang, Chaozai;Zhang, Huijun;Zhang, Xingquan;Zhu, Siyu [European Journal of Medicinal Chemistry,2020,vol. 200] Location in patent:supporting information

626-19-7 Synthesis