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Volume 2002
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10.3390/M285
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Short Note

2-(2-Hydroxy-5-methyl-3-formylphenyl)-imidazo[4,5-f][1,10]-phenanthroline

by
Hui Chao
*,
Cai-Wu Jiang
,
Xian-Lan Hong
and
Liang-Nian Ji
*
State Key Laboratory of Optoelectronic Materials and Technologies / Department of Chemistry, Zhongshan University, Guangzhou 510275, P. R. China
*
Authors to whom correspondence should be addressed.
Molbank 2002, 2002(1), M285; https://doi.org/10.3390/M285
Submission received: 2 April 2002 / Accepted: 16 May 2002 / Published: 20 February 2003
Versions Notes

Molbank 2002 m285 i001
1,10-phenanthroline-5,6-dione was prepared by a previously published method [1]. A mixture of 2-hydroxy- 5-methyl-isophthalic aldehyde (0.25 g, 1.5 mmol), 1,10-phenanthroline-5,6-dione (0.32 g, 1.5 mmol), ammonium acetate (2.31 g, 30 mmol) and glacial acetic acid (30 cm3) was refluxed for about 2 h, then cooled to room temperature and diluted with water (ca, 60 cm3). Dropwise addition of concentrated aqueous ammonia gave a yellow precipitate, which was collected and washed with water. The crude product in ethanol was purified by silica gel filtration (60-100 mesh, ethanol). The principal yellow band was collected. A yellow crystalline solid was obtained by slow evaporation of the solution, which was then dried in vacuo. Yield 0.35 g, 65%.
1H NMR (500 MHz, d6-DMSO): d13.85 (s, 1H), 10.51 (s, 1H), 9.14 (s, 1H), 8.99 (d, 2H, J = 8), 8.87 (d, 2H, J = 8), 8.29 (s, 1H), 7.78 (t, 2H, J = 7), 7.48 (s, 1H). 2.36 (s, 3H).
13C NMR (125 MHz, d6-DMSO): 192.2, 158.9, 150.8, 148.1, 143.6, 134.9, 131.8, 131.3, 129.8, 128.1, 127.6, 126.3, 123.6, 123.3, 120.5, 22.3.
IR (KBr. cm-1): 3416s, 3036m, 1693s, 1609m, 1560m, 1482m, 1356m, 1250s, 1131m, 1075s, 969s, 807s, 737s and 646s.
FAB-MS ([M+1]+): 355.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgement

Support for this research provided by the National Natural Science Foundation of China, the National Science Foundation of Guangdong Province and Research Fund of Royal Society of Chemistry U.K. is gratefully acknowledged.

References

  1. Yamada, M.; Tanaka, Y.; Yoshimato, Y.; Kuroda, S.; Shimao, I. Bull. Chem. Soc. Jpn. 1992, 65, 1006. [CrossRef]

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MDPI and ACS Style

Chao, H.; Jiang, C.-W.; Hong, X.-L.; Ji, L.-N. 2-(2-Hydroxy-5-methyl-3-formylphenyl)-imidazo[4,5-f][1,10]-phenanthroline. Molbank 2002, 2002, M285. https://doi.org/10.3390/M285

AMA Style

Chao H, Jiang C-W, Hong X-L, Ji L-N. 2-(2-Hydroxy-5-methyl-3-formylphenyl)-imidazo[4,5-f][1,10]-phenanthroline. Molbank. 2002; 2002(1):M285. https://doi.org/10.3390/M285

Chicago/Turabian Style

Chao, Hui, Cai-Wu Jiang, Xian-Lan Hong, and Liang-Nian Ji. 2002. "2-(2-Hydroxy-5-methyl-3-formylphenyl)-imidazo[4,5-f][1,10]-phenanthroline" Molbank 2002, no. 1: M285. https://doi.org/10.3390/M285

APA Style

Chao, H., Jiang, C. -W., Hong, X. -L., & Ji, L. -N. (2002). 2-(2-Hydroxy-5-methyl-3-formylphenyl)-imidazo[4,5-f][1,10]-phenanthroline. Molbank, 2002(1), M285. https://doi.org/10.3390/M285

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