HETEROCYCLES, Vol. 73, 2007
601
Anal. Calcd for C17H16N2: C, 82.22; H, 6.49 ; N, 11.28 . Found: C, 81.44 ; H, 6.42 ; N, 11.27.
7-(o-Fluoroanilino)-5,8-dimethylisoquinoline (8b) The same palladium-catalyzed coupling above p
was used as for compound (8a), such that 67 % of 8b was isolated. mp 152.3~153.0 ℃, 1H-NMR (500
MHz, CDCl3):δ9.38 (1H, s, CH arom.), 8.46 (1H, d, CH arom. J=6.0 Hz), 7.64 (1H, d, CH arom. J=6.0
Hz), 7.38 (1H, s, CH arom.), 7.05 (1H, t, CH arom. J=7.5 Hz), 6.91 (1H, t, CH arom. J=7.5 Hz), 6.78~
6.73 (2H, m, CH arom.), 5.66 (1H, s, NH), 2.56 (3H, s, CH3), 2.54(3H, s, CH3); MS (FAB) (m/z): 267
[M+1]+
Anal. Calcd for C17H15FN2: C, 76.67 ; H, 5.68 ; N, 10.52. Found: C, 76.43 ; H, 5.72 ; N, 10.60 .
7-(o-Chloroanilino)-5,8-dimethylisoquinoline (8c) The same palladium-catalyzed coupling above
was used as for compound (8a), such that 52 % of 8c was isolated. mp 165.8~166.3 ℃, 1H-NMR (500
MHz, CDCl3):δ9.48 (1H, s, CH arom.), 8.54 (1H, d, CH arom. J=5.5 Hz), 7.76 (1H, d, CH arom. J=5.5
Hz), 7.47 (1H, s, CH arom.), 7.39 (1H, d, CH arom. J=8.5 Hz), 7.09 (1H, t, CH arom. J=8.5 Hz), 6.82
(1H, t, CH arom. J=8.5 Hz), 6.75 (1H, d, CH arom. J=8.5 Hz), 6.07 (1H, s, NH), 2.64 (3H×2, s, CH3);
MS (FAB) (m/z): 283 [M+1]+
Anal. Calcd for C17H15ClN2: C, 72.21; H, 5.35 ; N,9.91. Found: C, 72.04 ; H, 5.32 ; N, 9.59 .
7-(o-Methylanilino)-5,8-dimethylisoquinoline (8d) The same palladium-catalyzed coupling above
1
was used as for compound (8a), such that 34% of 8e was isolated. mp 164.0~165.0 ℃, H-NMR (500
MHz, CDCl3):δ9.41 (1H, s, CH arom.), 8.36 (1H, d, CH arom. J=6.0 Hz), 7.72 (1H, d, CH arom. J=6.0
Hz), 7.26 (1H, s, CH arom.), 7.18 (1H, d, CH arom. J=7.5 Hz), 7.08 (1H, t, CH arom. J=7.5 Hz), 6.92
(1H, t, CH arom. J=7.5 Hz), 6.85 (1H, d, CH arom. J=7.5 Hz), 5.41 (1H, s, NH), 2.53 (3H, s, CH3), 2.51
(3H, s, CH3), 2.24(3H, s, CH3); MS (FAB) (m/z): 263 [M+1]+
Anal. Calcd for C18H18N2: C, 82.41; H, 6.92 ; N, 10.68. Found: C, 82.11 ; H, 6.67 ; N, 10.58 .
7-(m-Methylanilino)-5,8-dimethylisoquinoline (8e)
The same palladium-catalyzed coupling
procedure above was used as for compound (8a), such that 52% of 8f was isolated. mp 152.3~153.0 ℃,
1H-NMR (500 MHz, CDCl3):δ9.43 (1H, s, CH arom.), 8.49 (1H, d, CH arom. J=6.0 Hz), 7.69 (1H, d,
CH arom. J=6.0 Hz), 7.47 (1H, s, CH arom.), 7.15 (1H, t, CH arom. J=7.5 Hz), 6.75 (1H, d, CH arom.
J=7.5 Hz), 6.72~6.71 (2H, m, CH arom.), 5.62 (1H, s, NH), 2.59 (3H×2, s, CH3), 2.31 (3H, s, CH); MS
(FAB) (m/z): 263 [M+1]+
Anal. Calcd for C18H18N2: C, 82.41; H, 6.92 ; N, 10.68. Found : C, 82.09 ; H, 6.59 ; N, 10.82.
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