Dimethylformamide → HCID 67740547, compound

HRID 1708040Notes

Reaction equation

HRID 1708040 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-6d57d11b956745eaa4fe7a9de92c5bcc
Source dataset
uspto-grants-1994_10
Patent number
US05356906

Reaction notes

Loading…