p-Fluoronitrobenzene → 4-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

HRID 1465192Notes

Reaction equation

HRID 1465192 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[OH:15].F[C:17]1[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=1>>[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:17]1[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=1

Participants

3

Reactant 2

HCID 9590p-FluoronitrobenzeneHCID 178486804HCID 178486804, compound

Product 1

HCID 115945434-[(6,7-Dimethoxyquinolin-4-yl)oxy]aniline

Procedure

L1 was prepared from 6,7-dimethoxyquinolin-4-ol and 4-fluoro-nitrobenzene following the general procedure reported in Preparative Example 1 Step 1-2. 1H NMR (400 MHz, d6-DMSO, 300K) δ 3.91 (s, 3H), 3.92 (s, 3H), 5.16 (br s, 2H), 6.36 (d, J=5.3 Hz, 1H), 6.65 (d, J=8.8 Hz, 2H), 6.91 (d, J=8.8 Hz, 2H), 7.34 (s, 1H), 7.49 (s, 1H), 8.41 (d, J=5.3 Hz, 1H). MS (ES) C17H16N2O3 requires: 296. Found: 297 (M+H)+.

Sources & evidence

ORD record
ord-1fa6af77a0114be7aa38840b88051279
Source dataset
uspto-grants-2015_04
Patent number
US08999982B2

Reaction notes

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