HCID 22064916, compound → HCID 22064908, compound

HRID 1828048Notes

Reaction equation

HRID 1828048 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][N:10]2C(=O)C3C(=CC=CC=3)C2=O)[CH:5]=[CH:4][N:3]=1>C(O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 22064916HCID 22064916, compound

Product 1

HCID 22064908HCID 22064908, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-[2-(2-methyl-pyridin-4-yl)-ethyl]-isoindole-1,3-dione (2.58 g, 9.69 mmol) in 20 mL of ethanol was heated to reflux for 5 hours. The reaction was allowed to cool and stirred overnight. The resulting slurry was filtered and the filtrate was concentrated. The residue was dissolved in ethyl acetate and extracted several times with 10% aqueous hydrogen chloride solution. The aqueous layers were combined and neutralized with sodium carbonate and extracted with a mixture of chloroform and isopropanol (3:1). The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated to give the tile compound as a clear colorless oil. MS(ES): m/e (EI*) 137.1 [M+H]

Workup

  1. temperatureto reflux for 5 hours
  2. temperatureto cool
  3. filtrationThe resulting slurry was filtered
  4. concentrationthe filtrate was concentrated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. extractionextracted several times with 10% aqueous hydrogen chloride solution
  7. extractionextracted with a mixture of chloroform and isopropanol (3:1)
  8. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-4261a6ab3f8641378a37742d698c111f
Source dataset
uspto-grants-2006_06
Patent number
US07056937B2

Reaction notes

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