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

HRID 1640540Notes

Reaction equation

HRID 1640540 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 97.7%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of 8-bromomethyl-7-fluoro-2-methoxy-quinoline (32.03 g, 118.59 mmol) in acetone (460 mL) and water (585 mL) was treated with NaHCO3 (16.32 g, 194.28 mmol). The mixture was heated at reflux for 6 h. The volatiles were removed under reduced pressure and the aq. phase was extracted with EA (2×250 mL). The combined org. layers were washed with brine, dried over MgSO4 and concentrated to afford the title alcohol as a yellow oil (24 g, 97% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 6 h
  3. customThe volatiles were removed under reduced pressure
  4. extractionthe aq. phase was extracted with EA (2×250 mL)
  5. washlayers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8ef61daffbe648f7a1c34f7b12b95522
Source dataset
uspto-grants-2012_02
Patent number
US08114867B2

Reaction notes

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