6-Bromo-4-hydroxy-3-phenoxyquinolin-2(1H)-one → 6-Bromo-3-(4-chlorophenoxy)-N,N-diethyl-4-(trifluoromethyl)quinolin-2-amine

HRID 623963Notes

Reaction equation

HRID 623963 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=O)[C:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:5]2[C:21]([F:24])([F:23])[F:22].BrC1C=[C:28]2[C:33](=CC=1)[NH:32][C:31](=O)[C:30](OC1C=CC=CC=1)=C2O>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([N:32]([CH2:33][CH3:28])[CH2:31][CH3:30])[C:6]([O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:5]2[C:21]([F:24])([F:23])[F:22]

Participants

3

Reactant 2

HCID 867154446-Bromo-4-hydroxy-3-phenoxyquinolin-2(1H)-one2×HCID 867154486-bromo-3-(4-chlorophenoxy)-4-(trifluoromethyl)quinolin-2(1H)-one2×

Product 1

HCID 867154496-Bromo-3-(4-chlorophenoxy)-N,N-diethyl-4-(trifluoromethyl)quinolin-2-amine

Conditions

Temperature
60 °C

Procedure

The title compound was prepared using 6-bromo-2-chloro-3-(4-chlorophenoxy)-4-(trifluoromethyl)quinoline (Intermediate 7, step d) in place of 6-bromo-2,4-dichloro-3-phenoxyquinoline (Intermediate 5, step c) according to the procedure described in Intermediate 5, step d except the reaction mixture was heated at 60° C. under reflux condenser for 12 hours.

Workup

  1. temperatureunder reflux condenser for 12 hours

Sources & evidence

ORD record
ord-c7bd763717f44885b5976c4f9561b6f5
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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