Dimethylformamide → 2-[3-(Pyridin-3-yl)propyl]-1H-isoindole-1,3(2H)-dione

HRID 1708043Notes

Reaction equation

HRID 1708043 reaction equation
Br.[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10]Br)[CH:3]=1.CN(C)C=O.[C:17]1(=[O:27])[NH:21][C:20](=[O:22])[C:19]2=[CH:23][CH:24]=[CH:25][CH:26]=[C:18]12.[K].[OH-].[K+]>O>[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][CH2:10][N:21]2[C:17](=[O:27])[C:18]3[C:19](=[CH:23][CH:24]=[CH:25][CH:26]=3)[C:20]2=[O:22])[CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 127015693-(3-Bromopropyl)pyridine hydrobromideHCID 24194345Phthalimide potassium salt

Product 1

HCID 135575522-[3-(Pyridin-3-yl)propyl]-1H-isoindole-1,3(2H)-dioneYield 147.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7.9 g (28 mmoles) of 3-(3-pyridyl)-1-bromopropane HBr was added 150 mL of dimethylformamide and 27.0 g (145 mmoles) of potassium phthalimide. The reaction mixture was heated under reflux for 3 hours. The mixture was cooled, diluted with water, and made basic with aqueous potassium hydroxide. The product was then extracted with ethyl acetate, and the extracts were washed with saturated solutions of sodium bicarbonate and sodium chloride, dried and evaporated to give 11.0 g of 2-[3-(3-pyridinyl)propyl]-1H-isoindole-1,3(2H)-dione, m.p. 88°-90°; NMR (CDCl3) δ8.36-8.50 (m, 2H); 7.75-7.90 (m, 2H); 7.57-7.75 (m, 2H); 7.47-7.56 (d, 1H); 7.13-7.32 (m, 1H); 3.63-3.29 (t, 2H); 2.53-2.71 (t, 2H); 1.94-2.10 (m, 2H) .

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. extractionThe product was then extracted with ethyl acetate
  5. washthe extracts were washed with saturated solutions of sodium bicarbonate and sodium chloride
  6. customdried
  7. customevaporated

Sources & evidence

ORD record
ord-8b32b8afcfb64aa788227c997b9c0614
Source dataset
uspto-grants-1994_10
Patent number
US05356906

Reaction notes

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