Acetic Acid → HCID 15870503, compound

HRID 613002Notes

Reaction equation

HRID 613002 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[C:16]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:31][CH2:32][CH3:33])=[C:25]([O:28][CH2:29][CH3:30])[CH:26]=3)[CH:21]=[C:20]([CH2:34][O:35]C(=O)C)[C:19]=2[CH2:39][O:40]C(=O)C)[CH:15]=[CH:14][N:13]=1.C[O-].[Na+].C(O)(=O)C>CO>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]1[C:12]1[CH:17]=[C:16]([C:18]2[C:27]3[C:22](=[CH:23][C:24]([O:31][CH2:32][CH3:33])=[C:25]([O:28][CH2:29][CH3:30])[CH:26]=3)[CH:21]=[C:20]([CH2:34][OH:35])[C:19]=2[CH2:39][OH:40])[CH:15]=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium Methoxide2×HCID 15870500HCID 15870500, compound

Product 1

HCID 15870503HCID 15870503, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-[2-(1-oxo-1,2-dihydroisoquinolin-2-yl)-4-pyridyl]-2,3-bis(acetoxymethyl)-6,7-diethoxynaphthalene (1.84 g) in methanol (50 ml) is added sodium methoxide (0.52 g) under ice-cooling. The mixture is stirred at room temperature for 2.5 hours. To the mixture is added sodium methoxide (0.17 g) under ice-cooling, and the mixture is stirred at room temperature for one hour. Acetic acid (0.74 ml) is added to the reaction mixture under ice-cooling, and the mixture is concentrated under reduced pressure to remove the solvent. To the residue are added methylene chloride and an aqueous sodium hydrogen carbonate solution, and the methylene chloride layer is separated, washed, dried and concentrated under reduced pressure to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform:ethanol=25:1) to give 1-[2-(1-oxo-1,2-dihydroisoquinolin-2-yl)-4-pyridyl]-2,3-bis(hydroxymethyl)-6,7-diethoxynaphthalene (0.95 g) which is listed in Table 1.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. stirringthe mixture is stirred at room temperature for one hour
  4. temperaturecooling
  5. concentrationthe mixture is concentrated under reduced pressure
  6. customto remove the solvent
  7. additionTo the residue are added methylene chloride
  8. customan aqueous sodium hydrogen carbonate solution, and the methylene chloride layer is separated
  9. washwashed
  10. customdried
  11. concentrationconcentrated under reduced pressure
  12. customto remove the solvent
  13. customThe residue is purified by silica gel column chromatography (solvent; chloroform:ethanol=25:1)

Sources & evidence

ORD record
ord-bcdc1d5e9eea405fa543b85d95b01ea2
Source dataset
uspto-grants-1999_12
Patent number
US06005106

Reaction notes

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