4-Aminopyridine → HCID 12822541, compound

HRID 127288

Reaction equation

HRID 127288 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 12822541HCID 12822541, compound

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-aa672faddfbb46fe8114bfc5b5f4b947
Source dataset
uspto-grants-1981_03
Patent number
US04255429

Linked notes

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