Sodium Bicarbonate → HCID 67131029, compound

HRID 1916328Notes

Reaction equation

HRID 1916328 reaction equation
[Br:1][C:2]1[C:11]([CH2:12]Br)=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([O:14][CH3:15])=[N:9]2)=[CH:4][CH:3]=1.C([O-])(O)=[O:17].[Na+]>CC(C)=O.O>[Br:1][C:2]1[C:11]([CH2:12][OH:17])=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([O:14][CH3:15])=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 67131056HCID 67131056, compound

Product 1

HCID 67131029HCID 67131029, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A suspension of 7-bromo-8-bromomethyl-2-(methyloxy)quinoline (35.2 g; prepared according to WO 2007/081597; containing 20% of debrominated compound) in acetone/water (1:1; 860 mL) was refluxed for 6 h in presence of NaHCO3 (14.63 g). The org. solvent was removed under reduced pressure and the residue was extracted with EA. The org. layer was washed with brine and dried over Na2SO4. The solvent was then evaporated and the residue was crystallized from TBDME, affording an off-white solid (16.0 g; 56% yield).

Workup

  1. customsolvent was removed under reduced pressure
  2. extractionthe residue was extracted with EA
  3. washlayer was washed with brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was then evaporated
  6. customthe residue was crystallized from TBDME
  7. customaffording an off-white solid (16.0 g; 56% yield)

Sources & evidence

ORD record
ord-f9b8a55b01ca4149968070ca2b78f3a2
Source dataset
uspto-grants-2013_12
Patent number
US08618092B2

Reaction notes

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