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

HRID 1583435노트

반응식

HRID 1583435 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
130 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-518d8c847a6041faad2b4806ca7f7c40
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04551460

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