Hydrogen Bromide → 2-Benzyl-7-bromo-3-hydroxyquinoline

HRID 1359419Notes

Reaction equation

HRID 1359419 reaction equation
[CH2:1]([C:8]1[C:17]([O:18]C)=[CH:16][C:15]2[C:10](=[CH:11][C:12]([Br:20])=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br.C(=O)([O-])[O-].[K+].[K+]>[Br-].C([P+](CCCC)(CCCC)CCCC)CCCCCCCCCCCCCCC.C(O)(=O)C>[CH2:1]([C:8]1[C:17]([OH:18])=[CH:16][C:15]2[C:10](=[CH:11][C:12]([Br:20])=[CH:13][CH:14]=2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 11430Potassium CarbonateHCID 181823072-Benzyl-7-bromo-3-methoxyquinoline

Product 1

HCID 181822012-Benzyl-7-bromo-3-hydroxyquinolineYield 146.9%

Reagents, catalysts & solvents 2

HCID 84716Hexadecyltributylphosphonium bromideCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of 1.28 g of 2-benzyl-7-bromo-3-methoxyquinoline obtained in Example 209d, 990 mg of n-hexadecyl-tri-n-butylphosphonium bromide, 12 ml of 47% hydrobromic acid and 10 ml of acetic acid was heated under reflux for 12 hours. After cooling as it was, the reaction solution was slowly poured into an aqueous potassium carbonate solution and the mixture was extracted with diethyl ether. The organic phase was washed with brine and the solvent was removed, to give 1.8 g of the target compound (including n-hexadecyl-tri-n-butylphosphonium bromide) as a crude product.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 12 hours
  3. temperatureAfter cooling as it
  4. extractionthe mixture was extracted with diethyl ether
  5. washThe organic phase was washed with brine
  6. customthe solvent was removed

Sources & evidence

ORD record
ord-e1d3390c94dd4fab8de2ea774b2ce691
Source dataset
uspto-grants-2003_07
Patent number
US06599917B1

Reaction notes

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