Hydrogen Bromide → HCID 22995923, compound

HRID 1167188Notes

Reaction equation

HRID 1167188 reaction equation
[C:1]1([C:7]2[C:16]([CH3:17])=[CH:15][C:14]3[C:9](=[C:10]([O:18]C)[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br.C(=O)(O)[O-].[Na+]>>[C:1]1([C:7]2[C:16]([CH3:17])=[CH:15][C:14]3[C:9](=[C:10]([OH:18])[CH:11]=[CH:12][CH:13]=3)[N:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 229959242-Phenyl-3-methyl-8-methoxyquinoline

Product 1

HCID 22995923HCID 22995923, compoundYield 96.2%

Procedure

4.75 g of (19 mmol) of 2-phenyl-3-methyl-8-methoxyquinoline and 111 ml of 48% hydrobromic acid are placed in a 1 l round-bottomed flask. The mixture is brought to reflux for 18 h and cooled to ambient temperature. Sodium bicarbonate is added to basify the solution and extraction is carried out with ethyl ether. The organic phases are combined, dried over magnesium sulfate, filtered and evaporated under vacuum to provide 4.3 g of 2-phenyl-3-methyl-8-hydroxyquinoline in the form of an oil. (Yield: 77%)

Workup

  1. temperatureto reflux for 18 h
  2. extractionthe solution and extraction
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated under vacuum

Sources & evidence

ORD record
ord-3844ae9e85e34d2cae89e29d14c2d396
Source dataset
uspto-grants-2003_09
Patent number
US06617336B1

Reaction notes

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