O-Phenylenediamine → N-(2-aminophenyl)-6-(8-methylquinolin-4-yloxy)-1-naphthamide

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Reaction Steps

The title compound (37.7 mg, 90% yield) was prepared as a brown solid from 6-(8-methylquinolin-4-yloxy)-1-naphthoic acid (32.9 mg, 0.1 mmol) and o-phenylenediamine (43.2 mg, 0.4 mmol) by an analogous procedure to that described in example 16. 1H NMR (DMSO-d6) δ 2.76 (s, 3H, Ar—CH3), 4.97 (s, 2H, benzene-NH2), 6.64 (t, J=7.1 Hz, 1H, Ar—H), 6.78 (d, J=5.0 Hz, 1H, Ar—H), 6.82 (d, J=7.8 Hz, 1H, Ar—H), 6.99 (t, J=7.3 Hz, 1H, Ar—H), 7.38 (d, J=7.5 Hz, 1H, Ar—H), 7.55-7.58 (m, 2H, Ar—H), 7.65 (t, J=7.6 Hz, 1H, Ar—H), 7.71 (d, J=7.0 Hz, 1H, Ar—H), 7.87-7.89 (m, 2H, Ar—H), 8.07 (d, J=8.2 Hz, 1H, Ar—H), 8.20 (d, J=7.9 Hz, 1H, Ar—H), 8.44 (d, J=9.2 Hz, 1H, Ar—H), 8.76 (d, J=5.0 Hz, 1H, Ar—H), 9.84 (s, 1H, benzene-NH). LC-MS (m/z) 420 (M+1).

Provenance & Evidence