Pyridine → HCID 19751528, compound

HRID 847223Notes

Reaction equation

HRID 847223 reaction equation
[C:1](Cl)(Cl)=[O:2].[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[OH:14])([O-:7])=[O:6].N1C=CC=CC=1.C[Si](C)(C)[N:23]1[CH2:27][CH2:26][CH2:25][C:24]1=[O:28]>C1C=CC=CC=1>[N+:5]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[O:14][C:24]([N:23]1[CH2:27][CH2:26][CH2:25][C:1]1=[O:2])=[O:28])([O-:7])=[O:6]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6371PhosgeneHCID 69472-NitrophenolHCID 844611-(Trimethylsilyl)pyrrolidin-2-one

Product 1

HCID 19751528HCID 19751528, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent4×

Procedure

To a solution of phosgen (6.12 g, 61.8 mmol) in anhydrous benzene (30 ml) was dropwise added under ice-cooling a solution of 2-nitrophenol (8.60 g, 61.8 mmol) and purified pyridine (4.88 g, 61.8 mmol) in anhydrous benzene (20 ml). The mixture was stirred for 30 min. at room temperature. From the reaction solution were separated precipitates by filtration, and a filtrate was evaporated under reduced pressure to give a colorless oily material. The oily material was dissolved in anhydrous benzene (20 ml), to which was added a solution of 1-trimethylsilyl-2-pyrrolidinone (4.00 g, 25.4 mmol) in anhydrous benzene (10 ml). The mixture was stirred at room temperature for 30 min. The reaction mixture was evaporated under reduced pressure to dryness to give a solid material. The desired product was separated using column chromatography on silica gel (eluted with chloroform-acetone 30:1→3:1). Recrystallization from ethanol afforded 1.98 g of colorless prisms. Yield 31.1%

Workup

  1. customFrom the reaction solution were separated
  2. customprecipitates by filtration
  3. customa filtrate was evaporated under reduced pressure
  4. customto give a colorless oily material
  5. stirringThe mixture was stirred at room temperature for 30 min
  6. customThe reaction mixture was evaporated under reduced pressure to dryness
  7. customto give a solid material
  8. customThe desired product was separated
  9. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-ff9e4568f79a45969682c000ecae752f
Source dataset
uspto-grants-1992_08
Patent number
US05140041

Reaction notes

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