O-Phenylenediamine → HCID 49805131, compound

HRID 1510015Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][CH:7]=[C:6]2[O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[C:22]([C:26]([OH:28])=O)=[CH:21][CH:20]=[CH:19]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:26]([C:22]1[C:23]2[C:18](=[CH:17][C:16]([O:15][C:6]3[C:5]4[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)=[CH:25][CH:24]=2)[CH:19]=[CH:20][CH:21]=1)=[O:28]

Participants

Reactant 2

HCID 7243O-Phenylenediamine

HCID 248226036-(6,7-Dimethoxyquinolin-4-yloxy)-1-naphthoic acid

Product 1

HCID 49805131HCID 49805131, compoundYield 86%

Procedure

The title compound (40.0 mg, 86% yield) was prepared as a brown solid from 6-(6,7-dimethoxyquinolin-4-yloxy)-1-naphthoic acid (37.5 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 3.93 (s, 3H, —OCH3), 3.95 (s, 3H, —OCH3), 4.99 (s, 2H, benzene-NH2), 6.56 (d, J=5.2 Hz, 1H, Ar—H), 6.63 (t, J=7.6 Hz, 1H, Ar—H), 6.81 (d, J=7.6 Hz, 1H, Ar—H), 6.98 (t, J=7.2 Hz, 1H, Ar—H), 7.36 (d, J=7.6 Hz, 1H, Ar—H), 7.43 (s, 1H, Ar—H), 7.56-7.58 (m, 2H, Ar—H), 7.65 (t, J=7.6 Hz, 1H, Ar—H), 7.87-7.90 (m, 2H, Ar—H), 8.08 (d, J=8.0 Hz, 1H, Ar—H), 8.43 (d, J=9.2 Hz, 1H, Ar—H), 8.49 (d, J=5.2 Hz, 1H, Ar—H), 9.87 (s, 1H, benzene-NH). LC-MS (m/z) 466 (M+1).

Sources & evidence

ORD record: ord-0bf713d3327148ae9f33d60bd3170e97
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211901B2

Reaction notes

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