HCID 22326644, compound → 5-Quinolinol, 6-fluoro-2-methyl-

HRID 495440Notes

Reaction equation

HRID 495440 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([F:14])[C:8]=2[O:12]C)[N:3]=1>Br>[F:14][C:7]1[C:8]([OH:12])=[C:9]2[C:4](=[CH:5][CH:6]=1)[N:3]=[C:2]([CH3:1])[CH:11]=[CH:10]2

Participants

3

Reactant 1

HCID 22326644HCID 22326644, compound

Product 1

HCID 1355530195-Quinolinol, 6-fluoro-2-methyl-Yield 73%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

A mixture of 2-methyl-5-methoxy-6-fluoroquinoline (2.07 g, 10.8 mmol) and 48% hydrobromic acid (30 ml) was stirred at reflux for 24 h. The reaction mix was reduced to minimum volume in vacuo and partitioned between dichloromethane (50 ml) and sat. aqueous sodium bicarbonate solution (50 ml). The organic layer was dried over sodium sulfate, filtered and evaporated in vacuo to give the title compound as a brown solid (1.39 g, 73%).

Workup

  1. temperatureat reflux for 24 h
  2. additionThe reaction mix
  3. custompartitioned between dichloromethane (50 ml) and sat. aqueous sodium bicarbonate solution (50 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

Sources & evidence

ORD record
ord-cc1d97f25d5041eab976e0344acd29d2
Source dataset
uspto-grants-2005_09
Patent number
US06939871B2

Reaction notes

Loading…