718
Can. J. Chem. Vol. 87, 2009
General procedure for the synthesis of amidoalkyl
naphthols catalyzed by Yb(OTf)3 in ionic liquid
153.38, 169.79. HR-MS (EI): m/z calcd. for C19H16N2O4
336.1110; found: 337.1523 [M + H]+.
4-Chlorobenzaldehyde (103 mL, 1.49 mmol), b-naphthol
(110 mL, 1.49 mmol), acetamide (1.79 mmol), and Yb(OTf)3
(20 mol%, 46.2 mg) were added to a 10 mL round-bottom
flask containing the ionic liquid, [bmim][BF4] (3.0 mL).
The reaction mixture was stirred at 80 8C for 4 h in oil
bath. After completion of the reaction as indicated by TLC,
the reaction mixture was cooled to room temperature and
extracted with ethyl acetate – hexane (2 Â 5 mL, 4:1, v/v).
The ionic liquid, containing ytterbium triflate, was recovered
and dried under vacuum. The combined organic layer was
evaporated under reduced pressure. The product was recrys-
tallized from ethanol to give pure 4a (450 mg, 92%). The
product was characterized by 1H and 13C NMR, IR, and
mass spectroscopic data.
N-((2-Hydroxynaphthalen-1-yl)(4-nitrophenyl)-
methyl)acetamide (4e)
1H NMR (Me4Si; 400 MHz, DMSO-d6) d: 2.09 (s, 3H),
7.25–7.32 (m, 3H), 7.43 (t, J = 8.0 Hz, 1H), 7.46–7.49 (m,
3H), 7.82 (d, J = 8.0 Hz, 1H), 7.89 (brs, 1H), 8.16 (d, J =
8.0 Hz, 2H), 8.67 (d, J = 8.0 Hz, 1H), 10.22 (s, 1H). 13C
NMR (100 MHz, DMSO-d6) d: 22.53, 47.96, 117.91,
118.45, 122.58, 122.87, 123.19, 126.72, 127.13, 128.45,
128.67, 129.88, 132.23, 145.90, 151.22, 153.43, 169.84.
HR-MS (EI): m/z calcd. for C19H16N2O4 336.1110; found:
337.1476 [M + H]+.
Acknowledgement
This work was supported by Department of Science and
Technology, New Delhi (SR-FTP-CS-34–2007) and Council
of Scientific and Industrial Research (CSIR), New Delhi
(01(2214)/08/EMR-II). The author, IA, is thankful to Birla
Institute of Technology and Science, Pilani, for institutional
research fellowship.
Spectral data of selected amidoalkyl naphthols
N-((4-Chlorophenyl)(2-hydroxynaphthalen-1-yl)-
methyl)acetamide (4a)
1H NMR (Me4Si; 400 MHz, DMSO-d6) d: 2.02 (s, 3H),
7.14–7.32 (m, 7H), 7.39 (brs, 1H), 7.77–7.82 (m, 3H), 8.53
(s, 1H), 10.02 (s, 1H). 13C NMR (100 MHz, DMSO-d6) d:
22.61, 47.42, 117.67, 118.42, 122.42, 123.16, 124.62,
126.47, 127.03, 127.89, 128.45, 129.47, 130.64, 133.23,
141.78, 153.22, 169.45. HR-MS-EI: m/z calcd. for
C19H16ClNO2 325.0870; found: 326.1458 [M + H]+.
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