Water → 3,8-Dibromo-6-hydroxyquinoline

HRID 2421521Notes

Reaction equation

HRID 2421521 reaction equation
N[C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Br:12])[CH:11]=1)[N:8]=[CH:7][C:6]([Br:13])=[CH:5]2.[OH2:14]>P(=O)(O)(O)O.[Cl-].[Na+].O>[Br:13][C:6]1[CH:7]=[N:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([OH:14])=[CH:11][C:10]=2[Br:12]

Participants

5

Reactant 2

HCID 962WaterHCID 219231223,8-Dibromoquinolin-6-amine

Product 1

HCID 219231363,8-Dibromo-6-hydroxyquinoline

Reagents, catalysts & solvents 2

HCID 1004Phosphoric AcidSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
180 °C

Procedure

6-Amino-3,8-dibromoquinoline (1.1 g) was suspended in phosphoric acid (10 ml) containing water (10 ml) and heated in a sealed glass tube at 180° C. for 4 days. The mixture was cooled to ambient temperature, poured into brine and extracted with ethyl acetate. The organic extract was dried over magnesium sulphate, evaporated under reduced pressure and the residual solid fractionated by chromatography (silica; hexane/ethyl acetate) to give 3,8-dibromo-6-hydroxy-quinoline, 0.4 g, as a pale brown solid.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. extractionextracted with ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-964d48ceb25045b98dfe630832c0bb04
Source dataset
uspto-grants-2011_06
Patent number
US07956188B2

Reaction notes

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