6,7-Dimethoxy-4-(3-methoxy-4-nitrophenoxy)quinoline → 4-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methoxyaniline

HRID 573437Notes

Reaction equation

HRID 573437 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:21]=[CH:20][C:19]([N+:22]([O-])=O)=[C:18]([O:25][CH3:26])[CH:17]=1>CCO.CN(C=O)C>[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:21]=[CH:20][C:19]([NH2:22])=[C:18]([O:25][CH3:26])[CH:17]=1

Participants

3

Reactant 1

HCID 895815586,7-Dimethoxy-4-(3-methoxy-4-nitrophenoxy)quinoline

Product 1

HCID 218910314-((6,7-Dimethoxyquinolin-4-yl)oxy)-2-methoxyaniline

Reagents, catalysts & solvents 1

HCID 19794673N,N-dimethylformamide ethanolSolvent

Procedure

6,7-Dimethoxy-4-(3-methoxy-4-nitrophenoxy)quinoline was hydrogenated in EtOH/DMF using 10% Pd/C at 40 psi to yield 4-(6,7-dimethoxyquinolin-4-yloxy)-2-methoxy-phenylamine. LCMS m/z=327 (M+1); 1H NMR (DMSO) δ: 8.43 (d, 1H, J=6 Hz), 7.5 (s, 1H), 7.37 (s, 1H), 6.76 (d, 1H, J=2.6 Hz), 6.72 (d, 1H, J=9 Hz), 6.60 (dd, 1H, J=2.5, 8.5 Hz), 6.41 (d, 1H, J=5.6 Hz), 3.75 (s, 3H), 3.31 (s, 6H).

Sources & evidence

ORD record
ord-0a9b05c1530d4cfdbcf5141193fde9f9
Source dataset
uspto-grants-2015_05
Patent number
US09029538B2

Reaction notes

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