Reaction equation
[OH-:1].[K+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]2=O.[F:15][C:16]([F:28])([F:27])[C:17]1[CH:18]=[C:19]([C:23](=O)[CH2:24][CH3:25])[CH:20]=[CH:21][CH:22]=1>O.C(O)C>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:23]([C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([C:16]([F:15])([F:27])[F:28])[CH:18]=1)[C:24]([CH3:25])=[C:7]2[C:8]([OH:13])=[O:1]Participants
6
Conditions
- Temperature
- 85 °C
Procedure
Potassium hydroxide (29.8 g, 531 mmol) in water (49.2 mL) was added to an orange suspension of 5-bromoisatin (20 g, 88 mmol) in ethanol (172 mL). 1-[3-(Trifluoromethyl)phenyl]-1-propanone (19.68 g, 97 mmol) was added and the mixture was heated to 85° C. for 3 h. The solvent was removed under reduced pressure. The residue was diluted with water (400 mL) and stirred overnight. The aqueous mixture was cooled to 0° C. and adjusted to pH˜3 with concentrated HCl. The solid was collected by filtration and dried in a vacuum oven at 70° C. for 3 days to afford 6-bromo-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (42 g, >99% yield). This material was used without further purification. MS (m/z) 411.8 (M+H+).
Workup
- customThe solvent was removed under reduced pressure
- additionThe residue was diluted with water (400 mL)
- temperatureThe aqueous mixture was cooled to 0° C.
- filtrationThe solid was collected by filtration
- customdried in a vacuum oven at 70° C. for 3 days
Sources & evidence
- ORD record
- ord-c3533996947e4490825591d436c4c31f
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658636B2
Linked notes
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