Potassium Carbonate → Ethyl 1-(2-cyano-3-methylamino-4-nitrophenyl)-2-oxo-cyclopentanecarboxylate

HRID 1634243Notes

Reaction equation

HRID 1634243 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[C:6]([NH:10][CH3:11])[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][CH:3]=1.[O:15]=[C:16]1[CH2:20][CH2:19][CH2:18][CH:17]1[C:21]([O:23][CH2:24][CH3:25])=[O:22].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[NH4+].[Cl-]>[C:8]([C:7]1[C:6]([NH:10][CH3:11])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=[CH:3][C:2]=1[C:17]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:18][CH2:19][CH2:20][C:16]1=[O:15])#[N:9]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 112180896-Chloro-2-(methylamino)-3-nitrobenzonitrile

Product 1

HCID 12035481Ethyl 1-(2-cyano-3-methylamino-4-nitrophenyl)-2-oxo-cyclopentanecarboxylateYield 40.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

A mixture of 6-chloro-2-methylamino-3-nitrobenzonitrile (200 mg, 0.95 mmol) (Example 4), ethyl 2-oxocyclopentanecarboxylate (177 mg, 1.13 mmol) and K2CO3 (287 mg, 2.07 mmol) in DMF (5 mL) was stirred at room temperature for 60 h. The mixture was diluted with sat. NH4Cl solution and extracted with ether. The ethereal layer was washed with water and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography on silica (hexanes: EtOAc=3:1) to give ethyl 1-(2-cyano-3-methylamino-4-nitrophenyl)-2-oxo-cyclopentanecarboxylate (127 mg, 40%) as a yellow solid.

Workup

  1. extractionextracted with ether
  2. washThe ethereal layer was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography on silica (hexanes: EtOAc=3:1)

Sources & evidence

ORD record
ord-c1726e4f62de425c9d677ac805b5924a
Source dataset
uspto-grants-2003_01
Patent number
US06506769B2

Reaction notes

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