Water → HCID 18426852, compound

HRID 1281156Notes

Reaction equation

HRID 1281156 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH:12]([O:15][CH3:16])[O:13][CH3:14])[CH:6]=[CH:5]2.C([Li])CCC.CN(C)[CH:24]=[O:25].O>O1CCCC1>[CH3:14][O:13][CH:12]([O:15][CH3:16])[C:7]1[CH:6]=[CH:5][C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH:24]=[O:25])[CH:3]=2)[N:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 18426837HCID 18426837, compoundHCID 178418339Butyllithium

Product 1

HCID 18426852HCID 18426852, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromo-2-(dimethoxymethyl)quinoline (1.11 g, 3.94 mmol) in tetrahydrofuran (20 mL) were added n-butyllithium (1.6 mol/L; 3.7 mL, 5.9 mmol) and dimethylformamide (0.61 mL, 7.9 mmol) sequentially at −78° C. under nitrogen atmosphere, and the mixture was stirred for 10 min. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was combined, washed with brine and dried on anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (3:1 hexane/ethyl acetate) to afford 2-dimethoxymethyl-6-quinolinecarboxaldehyde (344 mg, 38%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried on anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography (3:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-358ecc24a31d4e8b9325780a25ca8fdb
Source dataset
uspto-grants-2002_09
Patent number
US06452014B1

Reaction notes

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