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

HRID 1510019Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[C:7]2[O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19]([C:23]([OH:25])=O)=[CH:18][CH:17]=[CH:16]2.[C:26]1([NH2:33])[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH2:32]>>[NH2:32][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[NH:33][C:23]([C:19]1[C:20]2[C:15](=[CH:14][C:13]([O:12][C:7]3[C:6]4[C:11](=[C:2]([CH3:1])[CH:3]=[CH:4][CH:5]=4)[N:10]=[CH:9][CH:8]=3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:25]

Participants

Reactant 2

HCID 7243O-Phenylenediamine

HCID 595905556-(8-Methylquinolin-4-yloxy)-1-naphthoic acid

Product 1

HCID 49805501N-(2-aminophenyl)-6-(8-methylquinolin-4-yloxy)-1-naphthamideYield 90%

Procedure

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).

Sources & evidence

ORD record: ord-4388475a0b1945e5b41e2cec58d311e3
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211901B2

Reaction notes

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