Methanol → HCID 21891575, compound

HRID 987427Notes

Reaction equation

HRID 987427 reaction equation
[BH4-].[Na+].[CH3:3][O:4][C:5]1[C:14]([O:15][CH3:16])=[C:13]([O:17][CH3:18])[CH:12]=[C:11]2[C:6]=1[CH:7]=[CH:8][C:9]([CH:19]=[O:20])=[N:10]2.CO>C1COCC1>[OH:20][CH2:19][C:9]1[CH:8]=[CH:7][C:6]2[C:11](=[CH:12][C:13]([O:17][CH3:18])=[C:14]([O:15][CH3:16])[C:5]=2[O:4][CH3:3])[N:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 1794248HCID 1794248, compoundHCID 4311764Sodium borohydride

Product 1

HCID 21891575HCID 21891575, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (418 mg) and 5,6,7-trimethoxyquinoline-2-carboaldehyde (2.14 g) were successively added to a mixed solvent of methanol (30 mL) and THF (30 mL) under ice cooling, and the mixture was stirred at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, and the residue was then extracted with ethyl acetate. The resultant organic layer was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After concentrating the organic layer under reduced pressure, the residue was purified by column chromatography on silica gel (chloroform:methanol=30:1) to obtain the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionthe residue was then extracted with ethyl acetate
  3. washThe resultant organic layer was washed with water and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationAfter concentrating the organic layer under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel (chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-77cf89ef638a4479ab51c377b163f0c3
Source dataset
uspto-grants-2003_10
Patent number
US06632810B2

Reaction notes

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