4-Aminopyridine → 3-Methyl-3-phenyl-1-(4-pyridyl)-pyrrolidin-2,5-dione

HRID 127284Notes

Reaction equation

HRID 127284 reaction equation
[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6](=[O:8])[O:5][C:3]1=O.[NH2:15][C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1.C1(C)C(C)=CC=CC=1>O>[CH3:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][C:6](=[O:8])[N:15]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[C:3]1=[O:5]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 7237O-XyleneHCID 49628343-Methyl-3-phenyloxolane-2,5-dione

Product 1

HCID 128225453-Methyl-3-phenyl-1-(4-pyridyl)-pyrrolidin-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 68.6 g of 2-methyl-2-phenylsuccinic anhydride, 34 g of 4-aminopyridine and 675 ml of xylene is refluxed on a water separator while stirring for 7 hours. It is cooled to 40°, filtered, cooled to 0° and filtered again. The second residue is recrystallized from isopropanol-hexane, to yield the 3-methyl-3-phenyl-1-(4-pyridyl)-pyrrolidin-2,5-dione melting at 90°-92°.

Workup

  1. customThe starting material is prepared
  2. temperatureIt is cooled to 40°
  3. filtrationfiltered
  4. temperaturecooled to 0°
  5. filtrationfiltered again
  6. customThe second residue is recrystallized from isopropanol-hexane

Sources & evidence

ORD record
ord-e9a1e971e5c948b295f5b816f0cff078
Source dataset
uspto-grants-1981_03
Patent number
US04255429

Reaction notes

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