Water → HCID 12701049, compound

HRID 1105689Notes

Reaction equation

HRID 1105689 reaction equation
[C:1]1(=[O:7])O[C:4](=[O:5])[CH2:3][CH2:2]1.[NH2:8][C:9]1[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=1.CS(O)(=O)=O.O>C1(C)C(C)=CC=CC=1>[N:12]1[CH:13]=[CH:14][C:9]([N:8]2[C:4](=[O:5])[CH2:3][CH2:2][C:1]2=[O:7])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 17274-AminopyridineHCID 6395Methanesulfonic AcidHCID 7922Succinic anhydride

Product 1

HCID 12701049HCID 12701049, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The starting material is prepared as follows: The mixture of 500 g of succinic acid anhydride, 471 g of 4-aminopyridine and 5,200 ml of xylene is heated to reflux while stirring and separating the water formed. After 30 minutes 15 ml of methane sulfonic acid are added and refluxing is continued until 5 moles of water are collected, requiring about 4 days. The mixture is cooled to room temperature, the supernatant is decanted off and the suspension combined with 1000 ml of isopropanol. It is stirred for 5 minutes, filtered, the residue washed with 250 ml of isopropanol and dried for 3 days under reduced pressure at room temperature and shortly at 50°, to yield the 1-(4-pyridyl)-pyrrolidin-2,5-dione melting at 232°-235°.

Workup

  1. customThe starting material is prepared
  2. temperatureis heated
  3. temperatureto reflux
  4. customseparating the water
  5. customformed
  6. temperaturerefluxing
  7. customare collected
  8. customthe supernatant is decanted off
  9. stirringIt is stirred for 5 minutes
  10. filtrationfiltered
  11. washthe residue washed with 250 ml of isopropanol
  12. customdried for 3 days under reduced pressure at room temperature and shortly at 50°

Sources & evidence

ORD record
ord-4f8463a50f4a43ed8bc497c37ad5b9fc
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

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