2-Methoxyethanol → HCID 22502472, compound

HRID 1251260Notes

Reaction equation

HRID 1251260 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[C:13]([C:21]3[CH:26]=[CH:25][N:24]=[C:23](Cl)[CH:22]=3)[N:12]=2)[CH2:7][CH2:6]1)[CH3:4].[CH3:28][O:29][CH2:30][CH2:31][OH:32]>>[CH2:3]([N:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH:14]=[C:13]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:32][CH2:31][CH2:30][O:29][CH3:28])[CH:22]=3)[N:12]=2)[CH2:7][CH2:6]1)[CH3:4]

Participants

4

Reactant 3

HCID 80192-MethoxyethanolHCID 24758Sodium hydrideHCID 22502633HCID 22502633, compound

Product 1

HCID 22502472HCID 22502472, compound

Procedure

60% oily sodium hydride (0.20 g) was added gradually to 2-methoxyethanol (50 ml), under ice-cooling. To the resulting solution was added 1-(4-ethylpiperazin-1-yl)-3-(2-chloropyridin-4-yl)isoquinoline (0.20 g) obtained in the previous Example, and the mixture was heated under reflux for 3 days. The reaction solution was evaporated, and to the resulting residue were added ethyl acetate and purified water. The ethyl acetate layer was washed with water and brine, and dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system), to give the title compound (0.12 g) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3 days
  4. customThe reaction solution was evaporated
  5. additionto the resulting residue were added ethyl acetate
  6. custompurified water
  7. washThe ethyl acetate layer was washed with water and brine
  8. dry with materialdried over magnesium sulfate
  9. customThe solvent was evaporated
  10. customthe resulting residue was purified by silica gel column chromatography (methylene chloride/methanol system)

Sources & evidence

ORD record
ord-ad66c7d82f5a45d9821124db144feeb7
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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