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

HRID 623967Notes

Reaction equation

HRID 623967 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7](Cl)[C:6]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:5]2[C:20]([F:23])([F:22])[F:21].BrC1C=[C:27]2[C:32](=CC=1)[NH:31][C:30](=O)[C:29](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:31]([CH2:32][CH3:27])[CH2:30][CH3:29])[C:6]([O:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[C:5]2[C:20]([F:23])([F:22])[F:21]

Participants

3

Reactant 2

HCID 867154446-Bromo-4-hydroxy-3-phenoxyquinolin-2(1H)-one2×HCID 867154526-Bromo-2-chloro-3-phenoxy-4-(trifluoromethyl)quinoline2×

Product 1

HCID 867154536-Bromo-N,N-diethyl-3-phenoxy-4-(trifluoromethyl)quinolin-2-amine

Conditions

Temperature
100 °C

Procedure

The title compound was prepared using 6-bromo-2-chloro-3-phenoxy-4-(trifluoromethyl)quinoline (Intermediate 8, step b) 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 100° C. under reflux condenser for 2.5 hours.

Workup

  1. temperatureunder reflux condenser for 2.5 hours

Sources & evidence

ORD record
ord-7fa3975b7116466a9fcbda1a187a624b
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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