4-Chloro-1,2-diaminobenzene → HCID 59590545, compound

HRID 1510003Notes

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][N: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.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([NH2:36])=[C:32]([NH2:37])[CH:31]=1>>[NH2:37][C:32]1[CH:31]=[C:30]([Cl:29])[CH:35]=[CH:34][C:33]=1[NH:36][C:26]([C:22]1[C:23]2[C:24](=[CH:25][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][N:7]=3)=[CH:17][CH:18]=2)[CH:19]=[CH:20][CH:21]=1)=[O:28]

Participants

Reactant 2

HCID 72634-Chloro-1,2-diaminobenzene

HCID 248237346-(6,7-Dimethoxyquinazolin-4-yloxy)-1-naphthoic acid

Product 1

HCID 59590545HCID 59590545, compoundYield 85.6%

Procedure

The title compound (42.9 mg, 83% yield) was prepared as a brown solid from 6-(6,7-dimethoxyquinazolin-4-yloxy)-1-naphthoic acid (37.6 mg, 0.1 mmol) and 4-chloro-o-phenylenediamine (17.1 mg, 0.12 mmol) by an analogous procedure to that described in example 16. 1H NMR (DMSO-d6) δ 4.01 (s, 6H, 2×OCH3), 5.31 (s, 2H, benzene-NH2), 6.65 (d, J=8.3 Hz, 1H, Ar—H), 6.86 (d, J=1.9 Hz, 1H, Ar—H), 7.41 (s, 1H, Ar—H), 7.58-7.67 (m, 4H, Ar—H), 7.89 (d, J=6.8 Hz, 1H, Ar—H), 8.01 (s, 1H, Ar—H), 8.09 (d, J=8.1 Hz, 1H, Ar—H), 8.37 (d, J=9.2 Hz, 1H, Ar—H), 8.55 (s, 1H, Ar—H), 9.84 (s, 1H, benzene-NH). LC-MS (m/z) 501 (M+1).

Sources & evidence

ORD record: ord-f7926616ecd24790b4879081027f7884
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08211901B2

Reaction notes

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