Potassium Carbonate → HCID 22727951, compound

HRID 2086070Notes

Reaction equation

HRID 2086070 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5](Cl)=[N:6][CH:7]=1.[NH2:12][C:13]1[CH:14]=[C:15]([N:19]2[CH2:23][CH2:22][CH2:21][C:20]2=[O:24])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCCl.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([N+:9]([O-:11])=[O:10])[C:5]([NH:12][C:13]2[CH:14]=[C:15]([N:19]3[CH2:23][CH2:22][CH2:21][C:20]3=[O:24])[CH:16]=[CH:17][CH:18]=2)=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 6839561-(3-Aminophenyl)pyrrolidin-2-oneHCID 70194125-Bromo-2-chloro-3-nitropyridine

Product 1

HCID 22727951HCID 22727951, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A suspension of 5-bromo-2-chloro-3-nitropyridine (3.79 g, 16 mmol), 1-(3-aminophenyl)pyrrolidin-2-one (2.56 g, 15 mmol) and potassium carbonate (2.0 g, 15 mmol) in 1,2-dichloroethane (25 ml) was heated at reflux for 60 hours. The reaction was cooled, diluted with dichloromethane (200 ml) and extracted with water. The organic phase was then dried over anhydrous sodium sulphate, filtered and pre-adsorbed on to silica (25 g). Purification by column chromatography eluting with isohexane on a gradient of ethyl acetate (10%-40%) gave 1-[3-(5-bromo-3-nitropyridin-2-ylamino)phenyl]pyrrolidin-2-one as a red solid (3.7 g, 68%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 60 hours
  3. temperatureThe reaction was cooled
  4. extractionextracted with water
  5. dry with materialThe organic phase was then dried over anhydrous sodium sulphate
  6. filtrationfiltered and pre-adsorbed on to silica (25 g)
  7. customPurification by column chromatography
  8. washeluting with isohexane on a gradient of ethyl acetate (10%-40%)

Sources & evidence

ORD record
ord-802ee8b24a2c4f088055f85035af65ec
Source dataset
uspto-grants-2004_04
Patent number
US06723735B1

Reaction notes

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