Ammonia → 1-[2-(2-Oxo-1,2-dihydroquinoxalin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene

HRID 324009Notes

Reaction equation

HRID 324009 reaction equation
[OH:1][C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].Br[C:15]1[CH:20]=[C:19]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[CH:24]=[C:23]([CH2:35][OH:36])[C:22]=2[CH2:37][OH:38])[CH:18]=[CH:17][N:16]=1.N>CN(C)C=O.[Cu]I.C(OCC)(=O)C>[O:1]=[C:2]1[CH:11]=[N:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:15]1[CH:20]=[C:19]([C:21]2[C:30]3[C:25](=[CH:26][C:27]([O:33][CH3:34])=[C:28]([O:31][CH3:32])[CH:29]=3)[CH:24]=[C:23]([CH2:35][OH:36])[C:22]=2[CH2:37][OH:38])[CH:18]=[CH:17][N:16]=1

Participants

8

Reactant 4

HCID 222AmmoniaHCID 24758Sodium hydrideHCID 106925601-(2-Bromo-4-pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthaleneHCID 178516710HCID 178516710, compound

Product 1

HCID 158723631-[2-(2-Oxo-1,2-dihydroquinoxalin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthaleneYield 19.2%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-hydroxyquinoxaline (2.92 g) in dimethylformamide (20 ml) is cooled with ice under nitrogen atmosphere, and thereto is added 60 % sodium hydride (0.78 g). The mixture is stirred at room temperature for 15 minutes, and thereto is added copper (I) iodide (4.19 g). The mixture is stirred at 120° C. for 15 minutes, and cooled to room temperature. To the mixture is added 1-(2-bromo-4-pyridyl)-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (2.02 g), and the mixture is stirred at 120° C. for five hours. After the reaction is complete, to the mixture are added ethyl acetate and aqueous ammonia, and the ethyl acetate layer is collected. The ethyl acetate layer is filtered, washed, dried, and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:methanol=20:1) to give 1-[2-(2-oxo-1,2-dihydroquinoxalin-1-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (450 mg), which is listed in Table 2.

Workup

  1. stirringThe mixture is stirred at 120° C. for 15 minutes
  2. temperaturecooled to room temperature
  3. stirringthe mixture is stirred at 120° C. for five hours
  4. customthe ethyl acetate layer is collected
  5. filtrationThe ethyl acetate layer is filtered
  6. washwashed
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customto remove the solvent
  10. customThe residue is purified by silica gel column chromatography (solvent; chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-a791a7fd4264485a9ca9f967ff8c3711
Source dataset
uspto-grants-2001_04
Patent number
US06214996B1

Reaction notes

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