Downstream synthetic route of Ferrocenecarboxylic acid

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocenecarboxylic acid,belong iron-catalyst compound

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO240,mainly used in chemical industry, its synthesis route is as follows.,1271-42-7

Triethylamine (0.1ml, 0.72mmol) was injected dropwise into the CH2Cl2 (40ml) suspension of carboxyferrocene 3 (0.5g, 2.17mmol) at 0C under N2 atmosphere. Oxalyl chloride (0.7ml, 8.2mmol) was then added dropwise into the solution. The reaction mixture was stirred at room temperature (r. t.) overnight. The solvent was then removed in vacuo, and the red solid residue, crude chlorocarbonylferrocene, was then dissolved in dry CH2Cl2 (20ml), added dropwise into the CH2Cl2 solution (10ml) of 9 (0.4g, 1.83mmol) and Et3N (1.5ml, 10.7mmol). The obtained mixture was further stirred overnight at r. t. under N2 atmosphere, and then washed successively with saturated NaHCO3 solution (1¡Á100ml) and distilled water (3¡Á100ml). The organic layer was dried with anhydrous Na2SO4, and vacuumed to provide the crude product 10 that was then purified by column chromatography with CH2Cl2/methanol (0%?5%) as the eluent and obtained as brown sticky oil. Yield: 0.7g, 89%. 1H NMR (400MHz, CDCl3, 25C, TMS), deltappm: 6.28 (t, J=9.3Hz, 1H, NHCO), 4.68 (t, J=3.8Hz, 2H, sub. Cp, Cp=eta [5]-C5H5), 4.32 (t, J=3.4Hz, 2H, sub. Cp), 4.19 (s, 5H, free Cp), 3.67-3.55 (m, 14H, 7¡ÁCH2), 3.36 (t, J=10.1Hz, 2H, CH2N3). 13C NMR (100MHz, CDCl3, 25C, TMS), deltappm: 170.4 (CONH), 70.8, 70.7, 70.4, 70.3, 69.8, 68.3 (Cp and CH2), 50.8 (CH2N3), 39.4 (NHCH2). MS (ESI, m/z), calcd. for C19H16O4N4Fe: 430.3; found: 453.1 (M+Na+). Selected IR (KBr, cm-1): 3335 (nuNH), 2869 (nuCH2), 2105 (nuN3), 1634 (nuC=O), 1539, 1453 (nuC=C, Cp), 1299 (nuC-N), 1106 (nuC-O-C), 823 (nuFeII).

With the complex challenges of chemical substances, we look forward to future research findings about Ferrocenecarboxylic acid,belong iron-catalyst compound

Reference£º
Article; Liu, Yue; Mu, Shengdong; Liu, Xiong; Ling, Qiangjun; Hang, Chaodong; Ruiz, Jaime; Astruc, Didier; Gu, Haibin; Tetrahedron; vol. 74; 37; (2018); p. 4777 – 4789;,
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