2-Chloro-1-fluoro-4-nitrobenzene → 3-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline

HRID 1465194Notes

Reaction equation

HRID 1465194 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].[Cl:16][C:17]1[CH:22]=[C:21]([N+:23]([O-])=O)[CH:20]=[CH:19][C:18]=1F>>[Cl:16][C:17]1[CH:22]=[C:21]([CH:20]=[CH:19][C:18]=1[O:15][C:6]1[C:5]2[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=2)[N:9]=[CH:8][CH:7]=1)[NH2:23]

Participants

3

Reactant 2

HCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 178486804HCID 178486804, compound

Product 1

HCID 117390273-Chloro-4-[(6,7-dimethoxy-4-quinolyl)oxy]aniline

Procedure

N1 was prepared from 6,7-dimethoxyquinolin-4-ol and 2-chloro-1-fluoro-4-nitrobenzene following the general procedure reported in Preparative Example 1 Step 1-2. 1H NMR (400 MHz, d6-DMSO, 300K) δ 3.92 (s, 6H), 5.45 (br s, 2H), 6.28 (d, J=5.3 Hz, 1H), 6.61 (dd, J=8.7 Hz, J=2.6 Hz, 1H), 6.78 (d, J=2.6 Hz, 1H), 7.07 (d, J=8.7 Hz, 1H), 7.36 (s, 1H), 7.50 (s, 1H), 8.42 (d, J=5.3 Hz, 1H). MS (ES) C17H16ClN2O3 requires: 330. Found: 331 (M+H)+.

Sources & evidence

ORD record
ord-f5582d08f96240d1be62cf2ea26a12d7
Source dataset
uspto-grants-2015_04
Patent number
US08999982B2

Reaction notes

Loading…