Dimethylformamide → HCID 67740547, compound

HRID 374454Notes

Reaction equation

HRID 374454 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.CN(C)C=O.[C@@H:14]12[C:23](=O)[O:22][C:20](=[O:21])[C@@H:15]1[CH2:16][CH2:17][CH2:18][CH2:19]2.[OH-].[K+]>O>[N:6]1[CH:7]=[CH:8][C:3]([CH2:2][N:1]2[C:20](=[O:21])[C@H:15]3[C@H:14]([CH2:19][CH2:18][CH2:17][CH2:16]3)[C:23]2=[O:22])=[CH:4][CH:5]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 773174-PyridinemethanamineHCID 641660Hexahydrophthalic anhydride, cis-

Product 1

HCID 67740547HCID 67740547, compoundYield 43.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 17.0 g (157 mmoles) of 4-aminomethylpyridine was added 40 mL of dimethylformamide and 24.2 g (157 mmoles) of cis-1,2-cyclohexanedicarboxylic anhydride. The mixture was heated under reflux for 2 hours. The cooled solution was diluted with water, made basic with aqueous potassium hydroxide, and extracted with ethyl acetate. The organic extracts were washed with saturated sodium bicarbonate solution and saturated sodium chloride solution, dried and evaporated to afford 16.8 g of 2-(4-pyridinylmethyl)-cis-3a,4,5,6,7,7a-hexahydro-1H-isoindole-1,3(2H)-dione, m.p. 91°-92°; NMR (CDCl3): δ8.53-8.63 (d, 2H); 7.19-7.29 (d, 2H); 4.63 (s, 2H); 2.80-3.00 (m, 2H); 1.78-2.00 (m, 2H); 1.63-1.78 (m, 2H); 1.33-1.58 (m, 4H).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic extracts were washed with saturated sodium bicarbonate solution and saturated sodium chloride solution
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-19d9e97ed3b644cb9835c91ac0861b7e
Source dataset
uspto-grants-1996_01
Patent number
US05480892

Reaction notes

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