Hydrogen Bromide → 7-Hydroxy-3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid
Reaction equation
[CH3:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([O:14]C)=[O:13])=[CH:9][C:8]([S:16]([CH3:19])(=[O:18])=[O:17])=[C:7]([O:20]C)[CH:6]=2.Br>C(O)(=O)C.O>[OH:20][C:7]1[CH:6]=[C:5]2[C:10]([C:11]([C:12]([OH:14])=[O:13])=[C:2]([CH3:1])[C:3]([C:22]3[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:30])([F:31])[F:29])[CH:23]=3)=[N:4]2)=[CH:9][C:8]=1[S:16]([CH3:19])(=[O:18])=[O:17]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of methyl 3-methyl-7-(methyloxy)-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (4.95 g, 10.92 mmol) and hydrobromic acid (30 mL, 552 mmol) in acetic acid (30 mL) was heated to reflux for 5 days. The mixture was cooled to room temperature and diluted with water. The solid precipitate was collected by filtration, washed with water, and air dried to afford 7-hydroxy-3-methyl-6-(methylsulfonyl)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (4.22 g, 91% yield). 1H NMR (400 MHz, DMSO-d6) δ14.51 (br. s., 1H), 11.77 (s, 1H), 8.32 (s, 1H), 7.95-8.00 (m, 2H), 7.90 (d, J=7.78 Hz, 1H), 7.78 (t, J=7.78 Hz, 1H), 7.54 (s, 1H), 3.41 (s, 3H), 2.36 (s, 3H); MS (m/z) 426.0 (M+H+).
Workup
- temperatureto reflux for 5 days
- filtrationThe solid precipitate was collected by filtration
- washwashed with water, and air
- customdried
Sources & evidence
- ORD record
- ord-c15c4a8008ea451ba5e8c73c7d5d7835
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658636B2
Reaction notes
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