Sodium Bicarbonate → (7-Fluoro-2-methoxy-quinolin-8-yl)-methanol

HRID 215802Notes

Reaction equation

HRID 215802 reaction equation
Br[CH2:2][C:3]1[C:4]([F:15])=[CH:5][CH:6]=[C:7]2[C:12]=1[N:11]=[C:10]([O:13][CH3:14])[CH:9]=[CH:8]2.C([O-])(O)=[O:17].[Na+]>CC(C)=O.O>[F:15][C:4]1[C:3]([CH2:2][OH:17])=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11]2)=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 667376508-(Bromomethyl)-7-fluoro-2-(methyloxy)quinoline

Product 1

HCID 66737655(7-Fluoro-2-methoxy-quinolin-8-yl)-methanolYield 73.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of 8-bromomethyl-7-fluoro-2-methoxy-quinoline (25 g, 92.56 mmol) in acetone (360 mL) and water (460 mL) was treated with NaHCO3 (12.74 g, 151.64 mmol, 1.6 eq.). The mixture was heated to reflux overnight. After cooling, the volatiles were removed in vacuo and the residue was partitioned between EA (300 mL) and water (100 mL). The aq. layer was extracted once with EA (250 mL) and the combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (Hept-EA 3:1) to afford the title alcohol as a yellowish solid (14.04 g).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. customthe volatiles were removed in vacuo
  5. customthe residue was partitioned between EA (300 mL) and water (100 mL)
  6. extractionThe aq. layer was extracted once with EA (250 mL)
  7. washlayers were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated to dryness
  11. customThe residue was purified by CC (Hept-EA 3:1)

Sources & evidence

ORD record
ord-14de19d544bc4822b065ea209f0a6539
Source dataset
uspto-grants-2012_06
Patent number
US08193179B2

Reaction notes

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