2-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridine → 3,4-Diethoxycarbonyl-5-nitro-6-phenyl-2-(p-tolylsulfonyl)pyridine

HRID 37505

Reaction equation

HRID 37505 reaction equation
Cl[C:2]1[C:7]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:6]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:5]([N+:18]([O-:20])=[O:19])=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:3]=1.O.O.O.O.[C:31]1([CH3:40])[CH:36]=[CH:35][C:34]([S:37]([O-:39])=[O:38])=[CH:33][CH:32]=1.[Na+]>C(O)C>[CH2:11]([O:10][C:8]([C:7]1[C:2]([S:37]([C:34]2[CH:35]=[CH:36][C:31]([CH3:40])=[CH:32][CH:33]=2)(=[O:39])=[O:38])=[N:3][C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:5]([N+:18]([O-:20])=[O:19])[C:6]=1[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:9])[CH3:12]

Participants

4

Reactant 2

HCID 199355872-Chloro-3,4-diethoxycarbonyl-5-nitro-6-phenylpyridineHCID 23690860Sodium 4-methylbenzene-1-sulfinate--water (1/1/4)

Product 1

HCID 199356083,4-Diethoxycarbonyl-5-nitro-6-phenyl-2-(p-tolylsulfonyl)pyridineYield 57.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.379 g of 2-chloro-3,4- diethoxycarbonyl-5-nitro-6-phenylpyridine, 0.5 g of sodium p-toluenesulfinate tetrahydrate and 15 ml of ethanol was heated under reflux for 3 hours. After concentration, the concentrate was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, and dried over sodium sulfate. After the solvent was distilled off, the residue was subjected to silica gel column chromatography with n-hexane/ethyl acetate (4:1) as the eluent. The eluate was concentrated to give crystals. The obtained crystals were recrystallized from the same solvent, to give 0.289 g of the title compound as colorless needles.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationAfter concentration
  4. extractionthe concentrate was extracted with ethyl acetate
  5. washThe extract was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over sodium sulfate
  7. distillationAfter the solvent was distilled off
  8. concentrationThe eluate was concentrated
  9. customto give crystals
  10. customThe obtained crystals were recrystallized from the same solvent

Sources & evidence

ORD record
ord-e8df5648462847aea31600732ea0cdf2
Source dataset
uspto-grants-1995_05
Patent number
US05420275

Linked notes

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