Sodium Bicarbonate → HCID 67131029, compound

HRID 527971Notes

Reaction equation

HRID 527971 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

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 67131056HCID 67131056, compound

Product 1

HCID 67131029HCID 67131029, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A suspension of 7-bromo-8-bromomethyl-2-methoxyquinoline (35.2 g; prepared according to WO 2007/081597) and NaHCO3 (14.63 g) in acetone (430 mL) and water (430 mL) was refluxed for 6 h. The org. solvent was removed under reduced pressure and the aq. layer was extracted twice with EA. The combined org. layers were sequentially washed with water and brine and dried over Na2SO4. The solvent was removed under reduced pressure and the residue was crystallized from TBDME, affording an off-white solid (16.01 g; 56% yield).

Workup

  1. temperaturewas refluxed for 6 h
  2. customsolvent was removed under reduced pressure
  3. extractionthe aq. layer was extracted twice with EA
  4. washlayers were sequentially washed with water and brine
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure
  7. customthe residue was crystallized from TBDME
  8. customaffording an off-white solid (16.01 g; 56% yield)

Sources & evidence

ORD record
ord-67dc006e497f4c6591da914b2b92263c
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

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