Water → 3,8-Dibromo-6-hydroxyquinoline

HRID 563890Notes

Reaction equation

HRID 563890 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-3bf10fc6f67444a582ea187600035eef
Source dataset
uspto-grants-2011_11
Patent number
US08067592B2

Reaction notes

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