, 1-naphthalenamine (4q) 4- Methoxy-1-naphthalenamine 31 and 4-methoxy-1-bromobenzene; 21 h; ethyl acetate/n-hexane 1:1; 96%; oil. IR ? 3380 (NH) cm ?1 . 1 H NMR (CDCl 3 ) ? 3, p.90
, Anal-Iodo-2-methoxyphenyl)-N-(4-methoxy)-1-naphthylamine (4r). 4-Methoxy-1-naphthalenamine 31 and 2,4-diiodoanisole; 48 h; flash chromatography ethyl acetate/n-hexane 1:20; 18%; oil, 51?7.58 IR ? 3390 (NH) cm ?1 . 1 H NMR (CDCl 3 ) ? 3.95 and 4.03 (2s, 6H, CH 3 ) benzene C3?H), 6.78 (d, 1H, J m = 2.0 Hz, benzene C6?H), pp.356182-356189
, 50 (m, 2H, naphthalene C6?H and C7?H), 7.92 and 8, pp.5-8
, 4-Methoxy-1-naphthalenamine 31 (9.1 mmol) and methyl 2-methoxy-5-bromobenzoate using (±) BINAP (0.76 mmol) Pd(OAc) 2 (0.51 mmol); 120 °C; 24 h; ethyl acetate/n-hexane 1:1; 97%; oil m, 2H, naphthalene H) Methyl 2-[(2-Methoxy-1-naphthyl)amino]benzoate (5c). 2-Me- thoxy-1-naphthalenamine 32 and methyl-2-bromobenzoate; 15.5 h (CO) cm ?1 . 1 H NMR (DMSO-d 6 ) ? 3, 1695 (CO) cm ?1 . 1 H NMR (CDCl 3 ) ? 3.88 (2s, 3H, CH 3 ), 3.89 (s, 3H, OCH 3 ), 4.04 (s, 3H, OCH 3 ), 5.60 (s broad, 1H, NH) 3 ), 3.89 (s, 3H, CH 3 ), 6.09 (m, 1H, benzene H), 6.66 (m, 1H, benzene H), 7.18 (m, 1H, naphthalene H), 7.35?7.45 (m, 2H, benzene H and naphthalene H), 7.57 (m, 1H, naphthalene H), 7.68 (m, 1H, benzene H), 7.88?7.95 (m, 3H, naphthalene H), 9.17 (s broad, 1H, NH). Anal. (C 19 H 17 NO 3 ) C, H, N. (1-Methoxy-2-naphthyl)phenylamine (6d). 1-Methoxy-2-naphtha- lenamine 33 and bromobenzene, p.1681, 0998.
, 1650 (CO) cm ?1 . 1 H NMR (DMSO-d 6 ) ? 4.01 (s, 3H, CH 3, pp.3400-3000
, 20 (m, 1H, naphthalene H), 8.54 (s broad, 1H, NH) Anal, pp.2-5
, 59 (s broad, 1H, NH), 12.32 (s broad, 1H, COOH) Anal General Procedure for the Synthesis of Compounds 4g,i?l, 5a,b, 6a?c, 7a, 8a, and 9a. A solution of the proper N-phenyl-1- naphthalenamine derivative 4m, pp.8-9
, Anal. (C 16 H 13 NO) C, H, N. 4-(4-Hydroxy-1-naphthylamino)benzoic Acid (4i). 4o; rt; 15 h; ethyl acetate/n-hexane 9:2; 45%; 214?217 °C; toluene, 50?7.57 IR ? 3360 (OH, NH), 2800 (COOH) cm ?1 . 1 H NMR Hz, naphthalene H), 7.50 (m, 2H, naphthalene H) 1H, naphthalene H), 8.45 (s broad, 1H, NH), 10.20 (s broad, 1H, OH), 12.15 (s broad, 1H, COOH). Anal. (C 17 H 13 NO 3 ) C, H, N. Methyl 4-(4-Hydroxy-1-naphthylamino)benzoate (4j). 4o; ?45 °C, p.502592
, Anal. (C 16 H 13 NO 2 ) C, H, N. 2-Hydroxy-5-(4-hydroxy-1-naphthylamino)benzoic Acid (4l). 4t; rt; 15 h; ethyl acetate; 17%; 175 °C (dec) IR ? 3350, 55?7.00 7.95?8.13 (m, 2H, naphthalene H), 8.67 and 9, pp.7-38
, Anal. (C 17 H 13 NO 4 ) C, H, N. 2-(2-Hydroxy-1-naphthylamino)benzoic Acid (5a) and Methyl 2-(2-Hydroxy-1-naphthylamino)benzoate (5b). 5c; rt; 23 min, Hz, naphthalene H), 7.20 (d, 1H, J m = 2.7 Hz, benzene C6? H), 7.44?7.49 (m, 2H, naphthalene C6?H and C7?H), 7.99 (m, 1H 1659 (CO) cm ?1 . 1 H NMR (DMSO-d 6 ) ? 6.09 (m, 1H, benzene H), 6.62 (m, 1H, benzene H), 7.14 (m, 1H, naphthalene H), 7.28?7.31 (m, 2H, naphthalene H), 7.39 (m, 1H benzene H), 7.62 (m, 1H, benzene H), p.829775, 2005.
, C 18 H 15 NO 3 ) C, H, N. 1-Hydroxy-N-phenylnaphthalen-2-amine (6a). 6d; ?45 °C
, 11 (m, 1H, naphthalene H) Anal. (C 16 H 13 NO) C, H, N. 4-(1-Hydroxy-2-naphthylamino)benzoic Acid (6b) and Methyl 4-(1-Hydroxy-2-naphthylamino)benzoate (6c). 6f; rt; 35 min; ethyl acetate/n-hexane 1:1. 6b: 45%; 210 °C (dec); methanol Anal, >300 °C. IR ? 3150 (NH and OH) cm ?1 . 1 H NMR 4H, benzene H and naphthalene H), 7.77 (m, 1H, naphthalene H) IR ? 3426 (OH and COOH)), 7.33?7.36 (m, 1H, naphthalene H), 7.42?7.50 (m, 3H, naphthalene H), 7.74?7.77 (m, 2H, benzene C3?H and C5?H), 7.84?7.86 (m, 1H, naphthalene H), 8.18 (s broad, 1H, NH), 8.19?8.21 (m, 1H, naphthalene H), 9.40 (s broad, 1H, OH), pp.6-81
, ethyl acetate/n-hexane 1:2. After isolation the compound 7a rapidly degraded so that no analytical and structural data are available
, Congo Red; IL, interleukin; ABBB, alizarin blue-black B
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