4-Hydroxybenzaldehyde → 4-(2-quinolinylmethoxy)Benzaldehyde

HRID 369422Notes

Reaction equation

HRID 369422 reaction equation
Cl.Cl[CH2:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1.[OH:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[CH:13][C:4]=1[CH2:3][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 1264-HydroxybenzaldehydeHCID 11430Potassium CarbonateHCID 30838232-(Chloromethyl)quinoline hydrochloride

Product 1

HCID 145789604-(2-quinolinylmethoxy)BenzaldehydeYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloromethylquinoline hydrochloride (6.42 g, 30 mmol), 4-hydroxybenzaldehyde (3.66 g, 30 mmol) and potassium carbonate (9.12 g, 66 mmol) were combined, to which 50 ml of DMF were added. The resulting mixture was stirred overnight at 90° C. The solvent was driven off under reduced pressure, the residue was extracted with ethyl acetate. The organic layer was washed with 1 N aqueous solution of sodium hydroxide and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure, whereby 7.19 g of the title compound were obtained (yield: 91%).

Workup

  1. additionwere added
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe organic layer was washed with 1 N aqueous solution of sodium hydroxide
  4. dry with materiala saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f7fe61a123447d3aa0c0d1a7700f7ac
Source dataset
uspto-grants-2000_10
Patent number
US06136848

Reaction notes

Loading…