Sodium Sulfite → 3,4-Diethoxycarbonyl-5-nitro-6-phenyl-2-sulfopyridine

HRID 37510

Reaction equation

HRID 37510 reaction equation
[S:1]([O-:4])([O-:3])=[O:2].[Na+].[Na+].Cl[C:8]1[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[C:12]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:11]([N+:24]([O-:26])=[O:25])=[C:10]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[N:9]=1>O.C(O)C>[CH2:17]([O:16][C:14]([C:13]1[C:8]([S:1]([OH:4])(=[O:3])=[O:2])=[N:9][C:10]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:11]([N+:24]([O-:26])=[O:25])[C:12]=1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:15])[CH3:18]

Participants

5

Reactant 2

HCID 24437Sodium SulfiteHCID 199355872-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine

Product 1

HCID 199356093,4-Diethoxycarbonyl-5-nitro-6-phenyl-2-sulfopyridineYield 59.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 0.28 g of sodium sulfite in 7 ml of water was added to a solution of 0.70 g of 2-chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine in 7 ml of ethanol, and the mixture was heated under reflux for minutes. After the reaction mixture was concentrated, the concentrate was acidified with 1N HCl, followed by extraction with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over magnesium sulfate. After concentration to dryness under reduced pressure, the residue was recrystallized from chloroform/ether, to give 0.47 g of white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for minutes
  3. concentrationAfter the reaction mixture was concentrated
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe extract was washed with an aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationAfter concentration to dryness under reduced pressure
  8. customthe residue was recrystallized from chloroform/ether

Sources & evidence

ORD record
ord-b90069235e134fd59f7501c27c3f1a71
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Linked notes

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