Sodium Hydroxide → HCID 22502866, compound

HRID 1251152Notes

Reaction equation

HRID 1251152 reaction equation
C([N:3]1[CH2:8][CH2:7][N:6]([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:10]=2)[CH2:5][CH2:4]1)=O.[OH-].[Na+]>C(O)C>[N:6]1([C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH:12]=[C:11]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[N:10]=2)[CH2:7][CH2:8][NH:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22502632HCID 22502632, compound

Product 1

HCID 22502866HCID 22502866, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1-(4-Formylpiperazinyl)-3-(4-methoxyphenyl)isoquinoline (4.797 g) was dissolved in ethanol (85 ml), followed by the addition of 2N sodium hydroxide (35 ml), and the mixture was heated under reflux for 4 hr. The reaction mixture was evaporated, water was added thereto, and extracted with chloroform. The resulting organic layer was washed with water, dried (over MgSO4) and evaporated. The resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a colorless solid (2.720 g, yield; 63%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hr
  3. customThe reaction mixture was evaporated
  4. additionwater was added
  5. extractionextracted with chloroform
  6. washThe resulting organic layer was washed with water
  7. dry with materialdried (over MgSO4)
  8. customevaporated
  9. customThe resulting residue was purified by (NH) silica gel column chromatography (ethyl acetate/hexane system)

Sources & evidence

ORD record
ord-c979ababf42b4ebd82fc258be4e2eacd
Source dataset
uspto-grants-2002_01
Patent number
US06340759B1

Reaction notes

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