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extract was washed with brine, dried over MgSO4, and
concentrated in vacuo. Purification of the residue by flash
column chromatography on silica gel (eluent: CH2Cl2/MeOH
) 40/1) gave 270 mg (85%) of 9 as a white solid; mp ) 87-89
°C. 1H NMR (300 MHz, CDCl3): δ 8.32 (d, J ) 9.3 Hz, 1H),
8.21 (s, 1H), 6.94 (d, J ) 2.4 Hz, 2H), 6.54 (t, J ) 2.4 Hz, 1H),
6.46 (m, 1H), 6.44 (s, 1H), 3.82 (s, 3H), 3.79 (s, 6H), 3.75 (s,
3H). 13C NMR (75 MHz, CDCl3): δ 164.76, 160.96, 156.55,
149.50, 137.71, 121.33, 120.67, 105.02, 103.85, 103.41, 99.66,
55.82, 55.61, 55.57. EIMS m/z: 317 (M+, 75%). Anal. (C17H19
-
NO5) C, H, N.
(3,5-Dim eth oxy-ben zylid en e)-(2,4-d im eth oxy-p h en yl)-
a m in e (11). A solution of 3,5-dimethoxy benzaldehyde (153
mg, 1 mmol) and 2,4-dimethoxyaniline (153 mg, 1 mmol) in
toluene (5 mL) was heated to reflux in a Dean and Stark
apparatus for 16 h. After the solvent was removed in vacuo,
the crude product was recrystallized from MeOH to give 151
mg (50%) of 11 as a light brown solid; mp ) 70-72 °C. 1H
NMR (300 MHz, CDCl3): δ 8.43 (s, 1H), 7.06 (d, J ) 2.4 Hz,
2H), 7.2 (d, J ) 8.4 Hz, 1H), 6.57-6.54 (m, 2H), 6.50 (dd, J )
2.7, 8.7 Hz, 1H), 3.88 (s, 3H), 3.86 (s, 6H), 3.83 (s, 3H). 13C
NMR (75 MHz, CDCl3): δ 159.5, 138.6, 134.8, 120.7, 115.1,
107.1, 107.0, 116.2, 104.3, 104.1, 103.8, 99.4, 99.3, 55.8, 55.7,
55.5, 55.4. EIMS m/z: 301 (M+, 100%). Anal. (C17H19NO4) C,
H, N.
Ack n ow led gm en t. This study was supported by a
grant from the Korea Health 21 R&D Project, Ministry
of Health and Welfare, Republic of Korea (HMP-00-CH-
15-0014).
Su p p or tin g In for m a tion Ava ila ble: 1H NMR spectra
and mass spectra of 7a , 7f, 7g, 7i, 7j, 9, and 11. This material
s.org.
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