Hydrogen Bromide → 7-Hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

HRID 245203Notes

Reaction equation

HRID 245203 reaction equation
Br.[CH3:2][C:3]1[C:4]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=2)=[N:5][C:6]2[C:11]([C:12]=1[C:13]([O:15]C)=[O:14])=[CH:10][C:9]([S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18])=[C:8]([O:23]C)[CH:7]=2>C(O)(=O)C.O>[OH:23][C:8]1[CH:7]=[C:6]2[C:11]([C:12]([C:13]([OH:15])=[O:14])=[C:3]([CH3:2])[C:4]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:34])[F:32])[CH:26]=3)=[N:5]2)=[CH:10][C:9]=1[S:17]([CH:20]([CH3:22])[CH3:21])(=[O:19])=[O:18]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 67383265Methyl 3-methyl-6-[(1-methylethyl)sulfonyl]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate

Product 1

HCID 1363383257-Hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acidYield 94.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Hydrobromic acid (80 mL, 1467 mmol) was added slowly to a solution of methyl 3-methyl-6-[(1-methylethyl)sulfonyl]-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylate (14.13 g, 29.3 mmol) in acetic acid (30 mL). The mixture was heated to reflux for 5 days. The mixture was cooled to room temperature and diluted with water. The solids were collected by filtration, washed with water, and dried to afford 7-hydroxy-3-methyl-6-[(1-methylethyl)sulfonyl]-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (12.5 g, 94% yield). 1H NMR (400 MHz, DMSO-d6) δ11.73 (br. s., 1H), 8.31 (s, 1H), 7.94-8.00 (m, 2H), 7.91 (d, J=7.78 Hz, 1H), 7.79 (t, J=7.65 Hz, 1H), 7.54 (s, 1H), 3.91 (dt, J=6.81, 13.74 Hz, 1H), 2.35 (s, 3H), 1.22 (s, 3H), 1.21 (s, 3H); MS (m/z) 454.1 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 5 days
  3. filtrationThe solids were collected by filtration
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-d0fe97055d2c4e5895bb92e96f7e6037
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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