Hydrochloric Acid → 5-Iodo-8-quinolinol

HRID 2356065Notes

Reaction equation

HRID 2356065 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[CH:9][CH:8]=[CH:7]2.[I-:12].[Na+].[OH-].[Na+].[O-]Cl.[Na+].Cl>CO>[I:12][C:5]1[CH:4]=[CH:3][C:2]([OH:1])=[C:11]2[C:6]=1[CH:7]=[CH:8][CH:9]=[N:10]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 19238-HydroxyquinolineHCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 23665760Sodium Hypochlorite

Product 1

HCID 961115-Iodo-8-quinolinol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 8-hydroxyquinoline (25.00 g, 172 mmol), sodium iodide (27.10 g, 181 mmol), and 6M NaOH (30.14 mL, 181 mmol) in methanol at 0° C. was treated with 5.25% aqueous NaOCl (13.46 g, 181 mmol) dropwise over 4 hours, stirred for 16 hours, adjusted to pH 7 with 6M HCl and pH 7 buffer, and extracted with 5% methanol in ethyl acetate (3×200 mL). The combined extracts were washed with brine (100 mL), dried (Na2SO4), filtered, and concentrated. The concentrate was dissolved in 10% methanol/ethyl acetate and filtered. The filtrate was dried (Na2SO4), filtered, and concentrated to provide the desired product.

Workup

  1. extractionextracted with 5% methanol in ethyl acetate (3×200 mL)
  2. washThe combined extracts were washed with brine (100 mL)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe concentrate was dissolved in 10% methanol/ethyl acetate
  7. filtrationfiltered
  8. dry with materialThe filtrate was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-5b8430ab917546d7b5dadb01f688645a
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

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