Paper
Organic & Biomolecular Chemistry
2.90 mmol), acetyl acetone (300 mg, 2.99 mmol), and 1 mL of
piperidine were dissolved in 30 mL of absolute dry ethanol.
After the solution was stirred at room temperature for 2 h, an
orange precipitate was separated out. The orange solid was fil-
tered and collected, and the product was crystallized from absol-
ute ethanol to afford the compound NAC (yield: 500 mg, 67%).
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1
Mp. 110–120 °C. H NMR (CDCl3, 300 MHz): δ (ppm): 8.13
(s, 1H), 8.04 (d, J = 9 Hz, 1H), 7.82 (q, J = 13.5 Hz, 2H), 7.58 (q,
J = 9 Hz, 1H), 7.42 (t, J = 7.5 Hz, 1H), 7.16 (d, J = 9 Hz, 1H),
5.15 (s, 1H), 2.57 (s, 3H), 1.85 (s, 3H). 13C NMR (CDCl3,
75 MHz): δ (ppm): 198.25, 152.78, 134.04, 130.77, 130.61,
130.35, 129.28, 129.02, 127.89, 124.49, 120.58, 118.10, 111.55,
99.49, 27.51, 26.42. HRMS (ESI-TOF): (m/z, %): [M + Na]+ calcd
for C16H14O3Na is 277.0841; Found: 277.0536; Elemental ana-
lysis: Calcd value: C, 75.57; H, 5.55; Observed value: C, 75.53;
H, 5.59.
Synthesis of the receptor NAC + N2H4 adduct (NAP). NAC
(300 mg, 1.18 mmol) was added to acetonitrile (20mL) and
stirred at room temperature to dissolve it to form a solution.
After sometime, hydrazine hydrate (60 mg, 1.18 mmol) was
added to it. The mixture was stirred for 10 minutes and after
checking the completion of the reaction by TLC, the crude
product was purified by silica gel column chromatography
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using 20% ethylacetate in pet-ether (v/v) to give a white com- 10 S. W. Thomas and T. M. Swager, Adv. Mater., 2006, 18,
pound NAP (150 mg, 50%). 1047.
Mp. 150–160 °C. 1H NMR (CDCl3, 300 MHz): δ (ppm): 11.88 11 (a) M. G. Choi, J. Hwang, J. O. Moon, J. Sung and
(s, 1H), 7.81(d, J = 9 Hz, 1H), 7.68 (t, J = 9.0 Hz, 1H), 7.44 (m,
1H), 7.22 (m, 2H), 7.06 (q, J = 7.5 Hz, 1H), 6.21 (s, 1H), 2.02 (s,
3H), 1.87 (s, 3H). 13C NMR (CDCl3, 75 MHz): δ (ppm): 155.81,
155.53, 132.29, 129.56, 128.82, 128.59, 126.31, 122.51, 121.71,
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119.81, 113.97, 112.90, 57.50, 25.36, 16.61, 10.98. HRMS 12 J. Fan, W. Sun, M. Hu, J. Cao, G. Cheng, H. Dong, K. Song,
(ESI-TOF): (m/z, %): [M + H]+ calcd for C16H14N2O is 251.1184;
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Acknowledgements
The authors thank the DST and CSIR (Govt. of India) for finan-
cial support. A.K.D. and acknowledge the CSIR for providing
fellowships.
Notes and references
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Org. Biomol. Chem.
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