Sodium Bicarbonate → HCID 67131029, compound

HRID 527969Notes

Reaction equation

HRID 527969 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-656417c120f74bfcb8af9d12c3a5757a
Source dataset
uspto-grants-2016_05
Patent number
US09346804B2

Reaction notes

Loading…