ORDER
REPRINTS
AMINONAPHTHALENE DERIVATIVES
2147
(CDCl3) ꢀ: 146.52, 134.86, 128.60, 127.15, 126.52, 126.03, 122.12, 116.23,
106.02, 60.41 (N-CH), 24.16 (CH3).
N-Phenyl-2-naphthylamine. Yield ¼ 68%, m.p. ¼ 98–101 ꢀC (108).9
Elemental anal. calcd. for C16H13N: C, 87.64; H, 5.98; N, 6.39; found: C,
87.42; H, 5.69; N, 6.31. 1H-NMR (CDCl3) ꢀ: 4.02 (s, 1H, NH); 6.70 (d, 2H,
J ¼ 7.66 Hz, Ho); 6.78 (t, 1H, J ¼ 7.37 Hz, Hp); 7.05 (d, 1H, J ¼ 2.49 Hz, H1);
7.08 (d, 1H, J ¼ 8.37 Hz, H3); 7.16 (t, 2H, J ¼ 7.83 Hz, Hm); 7.31 (t, 1H,
J ¼ 8.02 Hz, H6); 7.41 (t, 1H, J ¼ 7.94 Hz, H8); 7.64 (d, 1H, J ¼ 7.94 Hz, H5);
7.74 (m, 2H, H4, H8). 13C-NMR (CDCl3) ꢀ: 153.40, 145.92, 134.56, 129.75,
129.29, 128.84, 127.70, 126.43, 126.30, 123.50, 118.92, 117.77, 115.38,
109.45.
2-Methoxy-7-N,N-dimethylnaphthylamine.
69–70ꢀC. Elemental anal. calcd. for C13H15NO: C, 77.58; H, 7.51; N,
Yield ¼ 94%,
m.p. ¼
1
6.96; O, 7.95; found: C, 77.32; H, 7.25; N, 6.92. H-NMR (CDCl3) ꢀ: 3.01
(s, 6H, N-(CH3)2); 3.86 (s, 3H, O-CH3); 6.84 (m, 2H, H1, H8); 6.97 (m, 2H,
H3, H6); 7.55 (d, 1H, J ¼ 9.96 Hz, H5); 7.59 (d, 1H, J ¼ 9.25 Hz, H4). 13C-
NMR (CDCl3) ꢀ: 158.72, 150.23, 136.12, 129.45, 129.23, 124.63, 116.54,
115.46, 108.96, 104.75, 55.25, 40.65.
N,N,N0,N0-Tetramethyl-2,7-naphthalenediamine. Yield ¼ 95%, m.p. ¼
38–39 (40).10 Elemental anal. calcd. for C14H18N2: C, 78.46; H, 8.47; N,
13.07; found: C, 78.32; H, 8.58; N, 13.06. 1H-NMR (CDCl3) ꢀ: 3.07 (s, 12H,
CH3); 6.84 (d, 2H, J ¼ 2.34 Hz, H1, H8); 6.95 (dd, 2H, J ¼ 8.93 Hz, H3, H6);
7.59 (d, 2H, J ¼ 8.93 Hz, H4, H5) 13C-NMR (CDCI3) ꢀ:. 149.14, 136.35,
128.22, 120.62, 112.98, 105.50, 40.99 (N-CH3).
7-N,N-Dimethylamino-2-naphthol. Yield ¼ 66%, m.p. ¼ 130–131ꢀC.
Elemental anal. calcd. for C12H13NO: C, 76.98; H, 7.00; N, 7.48; O,
1
8.54; found: C, 76.83; H, 6.95; N, 7.23. H-NMR (CDCl3) ꢀ: 3.07 (s, 6H,
N-CH3); 5.25 (s, 1H, O-H); 6.78 (d, 1H, J ¼ 2.42 Hz, H8), 6.84 (dd, 1H,
J ¼ 8.70 Hz, J ¼ 2.90 Hz, H3); 6.95 (d, 1H, J ¼ 2.90 Hz, H1); 7.03 (dd, 1H,
J ¼ 9.02 Hz, J ¼ 2.42 Hz, H6); 7.51 (d, 1H, J ¼ 8.78 Hz, H5); 7.55 (d,
1H, J ¼ 9.12 Hz, H4). 13C-NMR (CDCl3) ꢀ: 154.07, 149.13, 136.20,
129.35, 128.56, 115.34, 114.14, 113.71, 107.96, 105.20, 40.84 (N-CH3).
7-Methoxy-2-naphthylamine. Yield ¼ 88%, m.p. ¼ 138ꢁ139ꢀC (143).11
Elemental anal. calcd. for C11H11NO: C, 76.28; H, 6.40; N, 8.09; O, 9.24;
1
found: C, 75.99; H, 6.27; N, 8.11. H-NMR (CDCl3) ꢀ: 3.78 (s, 2H, N-H2);
3.85 (s, 3H, O-CH3); 6.75 (dd, 1H, J ¼ 8.61 Hz, H3); 6.85 (m, 3H, H1, H6,
H8); 7.53 (m, 2H, H4, H5). 13C-NMR (CDCl3) ꢀ: 158.20, 144.20, 135.95,
129.55, 129.25, 124.33, 116.21, 115.21, 108.82, 104.68, 55.23 (O-CH3).
N,N-Dibutylaniline. Yield ¼ 90%, b.p. 160ꢀC (4 mm Hg) (269 (760 mm
Hg)). Elemental anal. calcd. for C14H23N: C, 81.89; H, 11.29; N, 6.82;
found: C, 81.70; H, 11.09; N, 7.04. 1H-NMR (CDCl3) ꢀ: 0.97 (m, 6H,
C-CH3); 1.32 (m, 4H, C-H3); 1.66 (m, 4H, C-H2); 2.74 (m, 4H, C-H1);