Potassium Iodide → 2-[6-(Quinolin-3-yl)hexyl]-1H-isoindole-1,3(2H)-dione

HRID 1583435Notes

Reaction equation

HRID 1583435 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Cl)[CH:2]=1.[C:18]1(=[O:28])[NH:22][C:21](=[O:23])[C:20]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:19]12.[K].[I-].[K+]>CN(C)C=O.O>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:22]2[C:18](=[O:28])[C:19]3[C:20](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:21]2=[O:23])[CH:2]=1

Participants

6

Reactant 3

HCID 4875Potassium IodideHCID 202605943-(6-Chlorohexyl)quinolineHCID 24194345Phthalimide potassium salt

Product 1

HCID 135575552-[6-(Quinolin-3-yl)hexyl]-1H-isoindole-1,3(2H)-dioneYield 82.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
130 °C

Procedure

A solution of 7.8 g of 3-quinolinehexanol in 35 ml of dry dichloromethane was treated dropwise with a solution of 6.07 g of thionyl chloride in 15 ml of dichloromethane. The reaction mixture was heated to reflux for 1 hour and evaporated to dryness. The residue was dissolved in dichloromethane, washed successively with water, saturated sodium bicarbonate solution and brine, dried over potassium carbonate and evaporated to give 8.3 g of crude 6-(3-quinolinyl)hexylchloride. A suspension of 8.3 g of 6-(3-quinolinyl)hexylchloride, 12.6 g of potassium phthalimide, and 0.50 g of potassium iodide in 60 ml of dimethylformamide was heated to a bath temperature of 130° C. for one hour. The cooled mixture was diluted with water and extracted with dichloromethane. The combined organic layers were washed with water, dried over potassium carbonate and evaporated. The crude solid was crystallized from ethyl acetate-hexane to give 9.9 g (82%) of 2-[6-(3-quinolinyl)hexyl]-1H-isoindole-1,3-(2H)-dione, mp 90°-91° C. An analytical sample was obtained from toluene, mp 95.5°-96.5° C.

Workup

  1. extractionextracted with dichloromethane
  2. washThe combined organic layers were washed with water
  3. dry with materialdried over potassium carbonate
  4. customevaporated
  5. customThe crude solid was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-518d8c847a6041faad2b4806ca7f7c40
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

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