O-Phenylenediamine → HCID 49805503, compound
Reaction equation
[F:1][C:2]([F:28])([F:27])[C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[CH:10][CH:9]=[C:8]2[O:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20]([C:24](O)=[O:25])=[CH:19][CH:18]=[CH:17]2.[C:29]1([NH2:36])[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[NH2:35]>>[NH2:35][C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[NH:36][C:24]([C:20]1[C:21]2[C:16](=[CH:15][C:14]([O:13][C:8]3[C:7]4[C:12](=[C:3]([C:2]([F:28])([F:1])[F:27])[CH:4]=[CH:5][CH:6]=4)[N:11]=[CH:10][CH:9]=3)=[CH:23][CH:22]=2)[CH:17]=[CH:18][CH:19]=1)=[O:25]Participants
Procedure
The title compound (38.3 mg, 81% yield) was prepared as a brown solid from 6-(8-trifluoromethylquinolin-4-yloxy)-1-naphthoic acid (39.8 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 4.98 (s, 2H, benzene-NH2), 6.65 (t, J=7.3 Hz, 1H, Ar—H), 6.83 (d, J=7.6 Hz, 1H, Ar—H), 6.89 (d, J=5.2 Hz, 1H, Ar—H), 7.00 (t, J=7.2 Hz, 1H, Ar—H), 7.38 (d, J=7.5 Hz, 1H, Ar—H), 7.62 (dd, J=2.4 and 9.2 Hz, 1H, Ar—H), 7.68 (t, J=7.7 Hz, 1H, Ar—H), 7.83 (t, J=7.9 Hz, 1H, Ar—H), 7.90 (d, J=7.0 Hz, 1H, Ar—H), 7.97 (d, J=2.3 Hz, 1H, Ar—H), 8.10 (d, J=8.3 Hz, 1H, Ar—H), 8.29 (d, J=7.1 Hz, 1H, Ar—H), 8.47 (d, J=9.2 Hz, 1H, Ar—H), 8.70 (d, J=7.8 Hz, 1H, Ar—H), 8.87 (d, J=5.2 Hz, 1H, Ar—H), 9.86 (s, 1H, benzene-NH). LC-MS (m/z) 474 (M+1).
Sources & evidence
- ORD record
- ord-b9f2f1c4ddb74d3883a8a83fc6d565ee
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211901B2
Reaction notes
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