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

HRID 1105682Notes

Reaction equation

HRID 1105682 reaction equation
[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])O[C:3]1=[O:4].[NH2:9][C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1.C1(C)C(C)=CC=CC=1>O>[CH3:1][CH:2]1[CH2:7][C:6](=[O:8])[N:9]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)[C:3]1=[O:4]

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 7237O-XyleneHCID 20051Methylsuccinic anhydride

Product 1

HCID 128225463-Methyl-1-(4-pyridyl)-pyrrolidin-2,5-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The starting material is prepared as follows: The mixture of 28.5 g of 2-methylsuccinic anhydride, 23.5 g of 4-aminopyridine and 350 ml of xylene is refluxed on a water separator while stirring for 3.5 hours. The hot solution is decanted from some gummy residue, cooled, filtered, the residue suspended in 100 ml of boiling isopropanol and filtered off again, to yield the 3-methyl-1-(4-pyridyl)-pyrrolidin-2,5-dione melting at 119°-120°.

Workup

  1. customThe starting material is prepared
  2. customThe hot solution is decanted from some gummy residue
  3. temperaturecooled
  4. filtrationfiltered
  5. filtrationfiltered off again

Sources & evidence

ORD record
ord-a004f31aed3945758b8cbbdfe5144491
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

Loading…