O-Phenylenediamine → HCID 59590542, compound
Reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([O:12][C:13]3[CH:14]=[C:15]4[C:20](=[CH:21][CH:22]=3)[C:19]([C:23](O)=[O:24])=[CH:18][CH:17]=[CH:16]4)=[CH:7][CH:8]=[N:9]2)=[CH:4][CH:3]=1.[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:6]3[C:5]4[C:10](=[CH:11][C:2]([Cl:1])=[CH:3][CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:22][CH:21]=2)[CH:16]=[CH:17][CH:18]=1)=[O:24]Participants
Procedure
The title compound (33.2 mg, 83% yield) was prepared as a brown solid from 6-(7-chloroquinolin-4-yloxy)-1-naphthoic acid (35.0 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 4.97 (s, 2H, benzene-NH2), 6.65 (t, J=7.4 Hz, Ar—H), 6.77 (d, J=5.5 Hz, 1H, Ar—H), 6.82 (d, J=7.2 Hz, 1H, Ar—H), 7.00 (t, J=7.0 Hz, 1H, Ar—H), 7.38 (d, J=7.2 Hz, 1H, Ar—H), 7.60 (dd, J=2.6 and 9.2 Hz, 1H, Ar—H), 7.67-7.74 (m, 2H, Ar—H), 7.89 (d, J=7.4 Hz, 1H, Ar—H), 7.94 (d, J=2.4 Hz, 1H, Ar—H), 8.09 (d, J=8.2 Hz, 1H, Ar—H), 8.13 (d, J=2.1 Hz, 1H, Ar—H), 8.41 (d, J=9.0 Hz, 1H, Ar—H), 8.46 (d, J=9.6 Hz, 1H, Ar—H), 8.76 (d, J=5.2 Hz, 1H, Ar—H), 9.85 (s, 1H, benzene-NH). LC-MS (m/z) 440 (M+1).
Sources & evidence
- ORD record
- ord-8f3ec5603c9c4d7db07bacb56ce29ef4
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08211901B2
Reaction notes
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