Water → HCID 67468998, compound

HRID 1019744Notes

Reaction equation

HRID 1019744 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[C:5]([O:11][CH3:12])=[CH:4][C:3]=1[CH:13](C(OC)=O)[C:14]([O:16][CH3:17])=[O:15].[Cl-].[Na+].O.CCOC(C)=O>CS(C)=O>[CH3:17][O:16][C:14](=[O:15])[CH2:13][C:3]1[CH:4]=[C:5]([O:11][CH3:12])[C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[Cl:1]

Participants

6

Reactant 4

HCID 962Water2×HCID 5234Sodium ChlorideHCID 8857Ethyl AcetateHCID 25156888HCID 25156888, compound

Product 1

HCID 67468998HCID 67468998, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of dimethyl 2-(2-chloro-5-methoxy-4-nitrophenyl)malonate (3.0 g, 9.44 mmol) and sodium chloride (0.99 g, 16.99 mmol) in DMSO (50 mL) and water (0.17 mL, 9.44 mmol) was heated for 5 hours at 120° C. The reaction mass was allowed to cool to room temperature and water (400 mL) and EtOAc (50 mL) were added and stirring continued for 15 minutes. The separated aqueous layer was extracted with EtOAc (50 mL), and then the combined organic layers were washed with brine (50 mL), dried (Na2SO4) and concentrated under reduced pressure. The crude residue was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane to give the desired material (1.5 g, 61%) as a solid.

Workup

  1. temperatureto cool to room temperature
  2. extractionThe separated aqueous layer was extracted with EtOAc (50 mL)
  3. washthe combined organic layers were washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customThe crude residue was purified by column chromatography on neutral silica gel using 15-25% EtOAc in hexane

Sources & evidence

ORD record
ord-91dc3740b6e44475ba29a840e1b9ed82
Source dataset
uspto-grants-2014_05
Patent number
US08716287B2

Reaction notes

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