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3-tert-butoxycarbonylamino-pyridine-2-carboxylic Acid Methyl Ester

Molbank 2009, 2009(1), M591; https://doi.org/10.3390/M591

Short Note
4-[(Pyridin-3-ylmethylene)amino]phenyloctadecanoate
1
Faculty of Engineering & Science, Universiti Tunku Abdul Rahman, Jln Genting Kelang, 53300 Kuala Lumpur, Setapak 53300 Kuala Lumpur, Malaysia
2
Liquid Crystal Research Laboratory, School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800 Minden, Penang, Malaysia
*
Author to whom correspondence should be addressed.
Received: 18 November 2008 / Accepted: 20 February 2009 / Published: 23 February 2009

Abstract

:
A new Schiff base 4-[(pyridin-3-ylmethylene)amino]phenyloctadecanoate was synthesized and its IR, 1H NMR, 13C NMR and MS spectroscopic data are presented.
Keywords:
4-[(Pyridin-3-ylmethylene)amino]phenyloctadecanoate; Schiff base, alkyl chain.
Schiff bases have received a considerable amount of attention from many researchers owing to their importance in exhibiting thermochromism and photochromism [1,2,3,4].
Molbank 2009 m591 i001
In analogy to a recently published procedure [5,6,7], a solution of 3-pyridinecarbaldehyde (4.28 g, 40 mmol) and 4-aminophenol (4.37g, 40 mmol) in absolute ethanol (70 mL) was heated under reflux for 3 hours. Schiff base 1 thus obtained was recrystallized from absolute ethanol. Then, Schiff base 1 (3.96 g, 20 mmol) in dimethylformamide (DMF) (4 mL), was added into a solution of stearic acid (5.69g, 20 mmol) and 4-dimethylaminopyridine (DMAP) (1.22 g, 10 mmol) in dichloromethane (70 mL). The resulting mixture was stirred in an ice bath. To this solution, N,N’-dicyclohexylcarbodiimide (DCC) (4.12 g, 20 mmol) dissolved in dichloromethane (20 mL) was added dropwise while stirring in the ice bath for an hour. The resulting mixture was subsequently stirred at room temperature for another 3 hours. Then, the reaction mixture was filtered and the excess solvent was removed from the filtrate by evaporation. Recrystallization from absolute ethanol gave the Schiff base 2 as gray solid (3.72g, 40%).
Melting Point: 92.2°C.
MS(EI): M+ (m/z) = 464
IR (KBr, cm-1): 2954, 2916, 2848 (C-H aliphatic); 1754 (C=O ester); 1626 (C=N); 1595, 1499 (C=C aromatic).
1H NMR (400 MHz, CDCl3): δ/ppm 0.89 (3H, t, CH3), 1.23-1.45 {m, 28H, CH3(CH2)14-}, 1.76 (qt, 2H, -CH2CH2COO-), 2.58 (t, 2H, -CH2COO-), 7.13 (d, 2H, Ar-H), 7.25 (d, 2H, Ar-H), 7.41 (dd, 1H, Ar-H), 8.28 (d, 1H, Ar-H), 8.50 (s, 1H, CH=N), 8.71 (dd, 1H, Ar-H), 9.01 (d, 1H, Ar-H).
13C NMR (100 MHz, CDCl3): δ/ppm 172.7 (COO), 157.6 (CH=N), 152.5, 151.4, 149.8, 149.3, 135.3, 132.2, 124.2, 122.7 and 122.2 (aromatic carbons), 34.8 (-CH2COO-), 25.3 (-CH2CH2COO-), 32.3, 30.1, 30.0, 29.9, 29.8, 29.7, 29.5, 25.3 and 23.1 (CH3(CH2)14-), 14.5 (CH3).
Elemental analysis: Calculated for C30H44N2O2: C, 77.54%, H, 9.54%, N, 6.03%; Found: C, 77.65%, H, 9.59%, N, 5.92%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

The authors would like to thank Universiti Tunku Abdul Rahman and Universiti Sains Malaysia for financial support and research facilities.

References and Notes

  1. Hadjoudis, E.; Vittorakis, M.; Moustakali-Mavridis, I. Tetrahedron 1987, 43, 1345–1360. [CrossRef]
  2. Hadjoudis, E.; Rontoyianni, A.; Ambroziak, K.; Dziembowska, T.; Mavridis, I.M. J. Photochem. Photobiol. A: Chem. 2004, 162, 521–530. [CrossRef]
  3. Oshima, A.; Momotake, A.; Arai, T. J. Photochem. Photobiol. A: Chem. 2004, 162, 473–479.
  4. Suzuki, T.; Arai, T. Chem. Lett. 2001, 124–125.
  5. Ha, S.T.; Ong, L.K.; Win, Y.F.; Koh, T.M.; Yeap, G.Y. Molbank 2008, (3), M582.
  6. Ha, S.T.; Ong, L.K.; Win, Y.F.; Koh, T.M.; Yeap, G.Y. Molbank 2009, (1), M584.
  7. Ha, S.T.; Ong, L.K.; Win, Y.F.; Koh, T.M.; Yeap, G.Y. Molbank 2009, (1), M585.
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