Water → 2-Trifluoromethylquinolin-8-ol

HRID 1384881Notes

Reaction equation

HRID 1384881 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([C:13]([F:16])([F:15])[F:14])[CH:9]=[CH:8]2.O.[OH-].[Na+]>Br>[F:16][C:13]([F:14])([F:15])[C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[C:3]([OH:2])[CH:4]=[CH:5][CH:6]=2)[N:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 614880HCID 614880, compound

Product 1

HCID 115720352-Trifluoromethylquinolin-8-olYield 99.1%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A solution of 8-methoxy-2-trifluoromethylquinoline (10.0 g) in 48% hydrobromic acid (40 ml) was stirred at reflux overnight. The reaction mixture was poured into water (200 ml) and the pH adjusted to 12.5 using 46-48% sodium hydroxide solution. After extraction with dichloromethane (2×25 ml) the aqueous layer was acidified to pH5.3 by the addition of 37% hydrochloric acid solution. The mixture was then extracted using dichloromethane (2×100 ml) and the combined organic extracts washed with water, dried over sodium sulfate, filtered and the solvent removed in vacuo to give the product (9.3 g) as a white solid.

Workup

  1. temperatureat reflux overnight
  2. extractionAfter extraction with dichloromethane (2×25 ml) the aqueous layer
  3. additionwas acidified to pH5.3 by the addition of 37% hydrochloric acid solution
  4. extractionThe mixture was then extracted
  5. washthe combined organic extracts washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b304b07e9fb74a8ab75f2725be463f52
Source dataset
uspto-grants-2001_07
Patent number
US06262070B1

Reaction notes

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