Benzene, 1-fluoro-2-methyl-4-nitro- → 4-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-aniline

HRID 1465193Notes

Reaction equation

HRID 1465193 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][C:18]=1[CH3:26]>>[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][C:18]=1[CH3:26]

Participants

3

Reactant 2

HCID 68001Benzene, 1-fluoro-2-methyl-4-nitro-HCID 178486804HCID 178486804, compound

Product 1

HCID 218911624-[(6,7-Dimethoxy-4-quinolyl)oxy]-3-methyl-aniline

Procedure

M1 was prepared from 6,7-dimethoxyquinolin-4-ol and 1-fluoro-2-methyl-4-nitrobenzene following the general procedure reported in Preparative Example 1 Step 1-2. 1H NMR (400 MHz, d5-DMSO, 300K) δ 1.93 (s, 3H), 3.92 (s, 6H), 5.06 (br s, 2H), 6.24 (d, J=5.2 Hz, 1H), 6.48 (dd, J=8.4 Hz, J=2.5 Hz, 1H), 6.53 (d, J=2.5 Hz, 1H), 6.83 (d, J=8.4 Hz, 1H), 7.35 (s, 1H), 7.53 (s, 1H), 8.40 (d, J=5.2 Hz, 1H). MS (ES) C19H19N2O3 requires: 310. Found: 311 (M+H)+.

Sources & evidence

ORD record
ord-199e61126c74414183d60dca8f16db13
Source dataset
uspto-grants-2015_04
Patent number
US08999982B2

Reaction notes

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