4-Ferrocenylaniline

Hu Ping, Ke-Qing Zhao* and Hong-Bo Xu

Department of Chemistry, Sichuan Normal University, Chengdu, 610066, China
Tel./Fax: 86-28-4764743. Email: [email protected] (Present e-mail: [email protected])

Received: 28 May 2001 / Accepted: 14 December 2001 /Published: 20 December 2001

Keywords: 4-nitrophenylferrocene, 4-ferrocenylaniline, reduction, metallomesogen, non-linear optical material, intermediate, tin

The reduction of 4-nitropheneylferrocene with tin in acidic condition gives 4-ferrocenylaniline, which is an important intermediate for the synthesis of ferrocene-containing Schiff's base liquid crystals [1].

To a stirred mixture of 4-nitrophenylferrocene [2] (2 g, 7 mmol) in 25 ml of concentrated hydrochloric acid and 40 ml ethanol is added tin (granulated, 4.5 g, 40 mmol) and the reaction mixture is heated under reflux for 4 h. After the mixture has cooled, 200 ml water is added and aqueous NaOH is added to adjust the pH to 14 before filtration. The filtrate is extracted with CH₂Cl₂ and dried (Na₂SO₄). The solvent is removed by rotary evaporation. The crude product is recrystallized from petroleum ether (boiling range 60-80^oC) to give 4-ferrocenylaniline as an red-orange solid (1.4 g, 76%).

M.p:  157-159^oC.

IR(KBr, cm^-1): 3437, 3350, 1621, 1605, 1529, 1454, 1103, 998.

¹HNMR(CDCl₃): 7.3(d, 2H, C₆H₄), 7.65(d, 2H, C₆H₄), 4.0(s, 5H, C₅H₅), 4.2(s, 2H, C₅H₄),

4.5(s, 2H, C₅H₄), 3.4(s, 2H, NH₂).

Elemental analysis for C₁₆H₁₅FeN: calculated, C, 68.57; H, 5.38; N, 5.00%. Found: C, 68.85; H, 5.46; N, 5.12%.

References

1. Espinet, P.; Esteruelas, M. A.; Oro, L. A.; Serrono, J. L.; Sola, E. Coor. Chem. Rev. 1992, 117, 215.
2. Hu, P.; Zhao, K.-Q.; Xu, H.B. Molecules 2001, 6, M249.

Sample Availability: Available from the authors and from MDPI.

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