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

HRID 1583435ノート

反応式

HRID 1583435 の反応式
[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

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
130 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-518d8c847a6041faad2b4806ca7f7c40
出典データセット
uspto-grants-1985_11
特許番号
US04551460

反応ノート

読み込み中…