Methanol → HCID 10782606, compound

HRID 324044Notes

Reaction equation

HRID 324044 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([C:22](O)=[O:23])[CH:9]=2)[CH:5]=[CH:4][N:3]=1.CO.[OH-].[Na+]>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[C:17]3[C:12](=[CH:13][C:14]([O:20][CH3:21])=[C:15]([O:18][CH3:19])[CH:16]=3)[CH:11]=[C:10]([CH2:22][OH:23])[CH:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22007447HCID 22007447, compound

Product 1

HCID 10782606HCID 10782606, compoundYield 24.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of 1-(2-chloro-4-pyridyl)-3-carboxy-6,7-dimethoxynaphthalene (2.3 g) in tetrahydrofuran (60 ml) is added dropwise a solution of sodium aluminum bis(2-methoxyethoxy) hydride (70% toluene solution, 2.36 ml) in tetrahydrofuran at −10° C., and the mixture is stirred at room temperature for one hour. To the mixture is added dropwise a solution of sodium aluminum bis(2-methoxyethoxy) hydride (70% toluene solution, 1.57 ml) in tetrahydrofuran (5 ml), and the mixture is heated with stirring at 40° C. for one hour. To the mixture is added methanol, and thereto is added an aqueous sodium hydroxide solution (sodium hydroxide (1.6 g) in water (20 ml)), and the mixture is stirred at 50° C. for 30 minutes. The reaction residue is extracted with ethyl acetate, and extracted with dichloromethane. The organic layer is washed with water, dried, and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:acetone=19:1), and crystallized from ether to give 1-(2-chloro-4-pyridyl)-3-hydroxymethyl-6,7-dimethoxynaphthalene (531 mg, yield; 24%).

Workup

  1. temperaturethe mixture is heated
  2. stirringwith stirring at 40° C. for one hour
  3. stirringthe mixture is stirred at 50° C. for 30 minutes
  4. extractionThe reaction residue is extracted with ethyl acetate
  5. extractionextracted with dichloromethane
  6. washThe organic layer is washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent; chloroform:acetone=19:1)
  11. customcrystallized from ether

Sources & evidence

ORD record
ord-800dabe364274a18bccbb7861daa3b16
Source dataset
uspto-grants-2001_04
Patent number
US06214996B1

Reaction notes

Loading…