Acetic Acid → HCID 15870504, compound

HRID 324007Notes

Reaction equation

HRID 324007 reaction equation
[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]1[C:11]1[CH:16]=[C:15]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=3)[CH:20]=[C:19]([CH2:31][O:32]C(=O)C)[C:18]=2[CH2:36][O:37]C(=O)C)[CH:14]=[CH:13][N:12]=1.C[O-].[Na+].C(O)(=O)C>CO>[O:1]=[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]1[C:11]1[CH:16]=[C:15]([C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=3)[CH:20]=[C:19]([CH2:31][OH:32])[C:18]=2[CH2:36][OH:37])[CH:14]=[CH:13][N:12]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 15870502HCID 15870502, compound

Product 1

HCID 15870504HCID 15870504, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-{2-[2-oxo-1,2-dihydro-5-nitropyridin-1-yl]-4-pyridyl}-2,3-bis(acetoxymethyl)-6,7-dimethoxynaphthalene (1.83 g) in methanol (50 ml) is added sodium methoxide (0.72 g) under ice-cooling. The mixture is stirred at room temperature for one hour. To the mixture is added acetic acid (0.8 ml) under ice-cooling, and the mixture is concentrated under reduced pressure to remove the solvent. To the residue are added chloroform and an aqueous sodium hydrogen carbonate solution, and the chloroform 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:acetone=3:1), and crystallized from ethyl acetate to give 1-{2-[2-oxo-1,2-dihydro-5-nitropyridin-1-yl]-4-pyridyl}-2,3-bis(hydroxymethyl)-6,7-dimethoxynaphthalene (0.81 g,) which is listed in Table 1.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. concentrationthe mixture is concentrated under reduced pressure
  4. customto remove the solvent
  5. additionTo the residue are added chloroform
  6. customan aqueous sodium hydrogen carbonate solution, and the chloroform layer is separated
  7. washwashed
  8. customdried
  9. concentrationconcentrated under reduced pressure
  10. customto remove the solvent
  11. customThe residue is purified by silica gel column chromatography (solvent; chloroform:acetone=3:1)
  12. customcrystallized from ethyl acetate

Sources & evidence

ORD record
ord-ebd9742701b64c2e997b699e7e4268ac
Source dataset
uspto-grants-2001_04
Patent number
US06214996B1

Reaction notes

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