Hydrogen Bromide → HCID 136338343, compound

HRID 245211Notes

Reaction equation

HRID 245211 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[O:12]C)[N:8]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[C:6]([CH3:24])=[C:5]2[C:25]([OH:27])=[O:26].Br>C(O)(=O)C.O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[N:8]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=1)[C:6]([CH3:24])=[C:5]2[C:25]([OH:27])=[O:26]

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 673840026-Fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid

Product 1

HCID 136338343HCID 136338343, compoundYield 99%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 6-fluoro-3-methyl-7-(methyloxy)-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (19.5 g, 51.4 mmol) in acetic acid (50 mL) was added hydrobromic acid (140 mL, 2.57 mol) slowly. The resulting mixture was heated to reflux for 5 days. The mixture was cooled to room temperature, diluted with water and filtered. The filter cake was washed with water and air dried to afford 6-fluoro-7-hydroxy-3-methyl-2-[3-(trifluoromethyl)phenyl]-4-quinolinecarboxylic acid (18.57 g, 99% yield). 1H NMR (400 MHz, DMSO-d6) δ14.27 (br. s., 1H), 11.04 (s, 1H), 7.90-7.95 (m, 2H), 7.87 (d, J=7.78 Hz, 1H), 7.76 (t, J=7.65 Hz, 1H), 7.50 (d, J=2.76 Hz, 1H), 7.47 (s, 1H), 2.34 (s, 3H); MS (m/z) 366.0 (M+H+).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 5 days
  3. filtrationfiltered
  4. washThe filter cake was washed with water and air
  5. customdried

Sources & evidence

ORD record
ord-f7e144b16d9346b183bb1c7c48d0917b
Source dataset
uspto-grants-2014_02
Patent number
US08658636B2

Reaction notes

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