4-Aminopyridine → 2-(4-Pyridyl)-hexahydroisoindole-1,3-dione

HRID 1105685Notes

Reaction equation

HRID 1105685 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[C@@H:8]12[C:17](=O)[O:16][C:14](=[O:15])[C@@H:9]1[CH2:10][CH2:11][CH2:12][CH2:13]2.CS(O)(=O)=O>C1(C)C(C)=CC=CC=1>[N:5]1[CH:6]=[CH:7][C:2]([N:1]2[C:14](=[O:15])[CH:9]3[CH:8]([CH2:13][CH2:12][CH2:11][CH2:10]3)[C:17]2=[O:16])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 17274-AminopyridineHCID 6395Methanesulfonic AcidHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 128225412-(4-Pyridyl)-hexahydroisoindole-1,3-dione

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

The starting material is prepared as follows: The mixture of 23.5 g of 4-aminopyridine, 38.5 g of cis-1,2-cyclohexanedicarboxylic acid anhydride and 400 ml of xylene is refluxed for 42 hours while stirring and separating the water formed. After the first half-hour, and after 18 hours, 1 ml of methane sulfonic acid is added to the mixture. It is filtered hot, the crystals formed after cooling are filtered off and recrystallized from isopropanol, to yield the 2-(4-pyridyl)-hexahydroisoindole-1,3-dione melting at 165°-168°.

Workup

  1. customThe starting material is prepared
  2. temperatureis refluxed for 42 hours
  3. customseparating the water
  4. customformed
  5. filtrationIt is filtered hot
  6. customthe crystals formed
  7. temperatureafter cooling
  8. filtrationare filtered off
  9. customrecrystallized from isopropanol

Sources & evidence

ORD record
ord-11ac26217ce145e6b16f56e2c3d4fcc7
Source dataset
uspto-grants-1982_01
Patent number
US04309541

Reaction notes

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