Next Article in Journal
Asymmetric Synthesis of a New Monocyclic β-Lactam as a potential biological active compound
Previous Article in Journal
Synthesis of 3,3´-[methylenebis(3,1-phenylenenitrilo)]bis[1,3-dihydro]-2H-indol-2-one as a novel bis-Schiff base
Open AccessShort Note

Synthesis of (4-chlorobenzylidene)-(2-chloropyridi-3-yl)amine

Department of Chemistry, College of Sciences, Shiraz University, Shiraz 71454, Iran
*
Author to whom correspondence should be addressed.
Molbank 2005, 2005(4), M438; https://doi.org/10.3390/M438
Received: 2 June 2005 / Accepted: 22 September 2005 / Published: 1 October 2005
Keywords: Schiff bases ; 3-amino-2-chloropyridine ; p-chlorobenzaldehyde ; biological activity Schiff bases ; 3-amino-2-chloropyridine ; p-chlorobenzaldehyde ; biological activity
Schiff bases are widely in use for synthetic purposes both by organic and inorganic chemists.1 They are used as biological, analytical, polymer and liquid crystalline materials.2 Schiff bases are reported to show a variety of biological activities such as antibacterial3,4,5, antifungal6,7, anticancer 8,9 and herbicidal 10 activities . Pyridinium compounds have biological activities11 such as antifungal12 and antibacterial12,13 activities. The presence of a chloro moiety in different types of compounds causes them to exhibit pesticidal activity.10
Molbank 2005 m438 i001
A mixture of 3-amino-2-chloro pyridine 1 (1.28 g, 10 mmol), 4-chlorobenzaldehyde 2 (1.40 g, 10 mmol) and anhydrous sodium sulfate (4.00 g) in dry dichloromethane (40.00 mL) was stirred at room temperature for seven hours. The suspension was filtered and washed with dichloromethane. The solvent was evaporated and new schiff base 3 was formed, which was washed with 10 mL acetic acid 5%, 10 mL NaHCO3 5% and water, successively, (2.04 g, 82 %).
Melting point: 54-56oC.
IR(KBr, cm-1): 1600.1 (CH=N); 1624.0 (C=N pyridine ring).
1H-NMR (250MHz, CDCl3): δ= 6.97-8.17 (7H, m, 2 Ph); 8.31 (1H, s, HC=N).
13C-NMR (62.9 MHz, CDCl3): δ= 123.55-146.49 (aromatic carbons); 162.55 (HC=N).
MS (m/z, %): 251 ([M+], 63.3); 250 (M-1, 100.0); 215 (C5H3NClN=CC6H4 , 14.8); 139 (C5H3NClN=C, 15.4); 112 (C5H3NCl, 52.2 ), 89 (C5H3NN, 19.4); 77 (C5H3N, 15.1).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgment

The authors thank the Shiraz University Research Council for financial support (Grant No. 83-GR-SC-31and 84-GR-SC-23 ).

References

  1. Arora, K.; Gupta, A.; Agarwall, D. D. Asian. J. Chem. 2002, 14, 1611.
  2. Tanaka, K.; Shiraishi, R. Green Chem. 2000, 2, 272.
  3. Shaikh kabeer, A.; Baseer, M. A.; Mote, N. A. Asian J. Chem. 2001, 13(2), 496.
  4. Pandeya, S. N.; Sriram, D.; Nath, G.; De Clercq, E. Il Farmaco 1999, 54, 624. [PubMed]
  5. El-masry, Afaf. H.; Fahmy, H. H.; Ali Abdelwahed, S. H. Molecules 2000, 5, 1429.
  6. More, P. G.; Bhalvankar, R. B.; Pattar, S. C. J. Indian Chem. Soc. 2001, 78, 474.
  7. Singh, W. M.; Dash, B. C. Pesticides 1988, 22(11), 33.
  8. Desai, S. B.; Desai, P. B.; Desai, K. R. Hetrocycl. Commun. 2001, 7(1), 83.
  9. Phatak, P.; Jolly, V. S.; Sharma, K. P. Orient. J. Chem. 2000, 16(3), 493.
  10. Samadhiya, S.; Halve, A. Orient. J. Chem. 2001, 17(1), 119.
  11. Sepcic, Kristina. J. Toxicol., Toxin Rev. 2000, 19(2), 139.
  12. Sliwa, W.; Mianowska, B. Hetrocycles 1989, 29(3), 557.
  13. Durta, I.; Dinica, R.; Bacu, E.; Anderi, M. Chem. Abstr. 2000, 132, 205326b.
  • Sample Availability: Available from MDPI.
Back to TopTop