6-Hydroxyquinoline → HCID 59885584, compound

HRID 843355Notes

Reaction equation

HRID 843355 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2.S(C1C=CC(C)=CC=1)(O[CH2:18][C@@H:19]1[O:21][CH2:20]1)(=O)=O>CN(C=O)C>[O:21]1[CH2:20][C@@H:19]1[CH2:18][O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[CH:9][CH:8]=[CH:7]2

Participants

5

Reactant 3

HCID 113746-HydroxyquinolineHCID 24758Sodium hydrideHCID 154187Glycidyl tosylate, (R)-

Product 1

HCID 59885584HCID 59885584, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
5 °C

Procedure

Sodium hydride (60 weight %; 0.36 g; 9.0 mmol) is washed with hexanes (3×5 mL) under an argon blanket. DMF (3 mL) is then added at ambient temperature and the stirred slurry is cooled to 5° C. A solution of 6-hydroxyquinoline (1.00 g; 6.9 mmol) in DMF (13 mL) is added dropwise over 10 minutes. The resulting mixture is allowed to warm to ambient temperature over 30 minutes affording a clear, reddish-brown solution. A solution of (R)-(−)-glycidyl tosylate (2.04 g; 9.0 mmol) in DMF (10 mL) is added dropwise over 10 minutes. The resulting mixture is stirred at ambient temperature for 13 hours, quenched by the addition of saturated aqueous ammonium chloride (5 mL), poured onto water (150 mL), and extracted with ether (3×75 mL). The combined ether layers are washed with saturated aqueous sodium bicarbonate (2×75 mL), then dried over MgSO4, filtered, and concentrated in vacuo. The residue is purified via silica gel chromatography with gradient elution (40%→70% ethyl acetate in hexanes) affording the desired product (0.94 g) as an oil. CIMS: MH+ 202.

Workup

  1. temperatureto warm to ambient temperature over 30 minutes
  2. customaffording a clear, reddish-brown solution
  3. customquenched by the addition of saturated aqueous ammonium chloride (5 mL)
  4. additionpoured onto water (150 mL)
  5. extractionextracted with ether (3×75 mL)
  6. washThe combined ether layers are washed with saturated aqueous sodium bicarbonate (2×75 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue is purified via silica gel chromatography with gradient elution (40%→70% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-56958230c0714d73b6ff31178c7377ff
Source dataset
uspto-grants-2002_04
Patent number
US06376514B1

Reaction notes

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