Thionyl Chloride → 3-(6-Chlorohexyl)quinoline

HRID 1583434ノート

反応式

HRID 1583434 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]O)[CH:2]=1.S(Cl)([Cl:20])=O>ClCCl>[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:20])[CH:2]=1

参加物

4

反応物 2

HCID 24386Thionyl ChlorideHCID 135575476-(Quinolin-3-YL)hexan-1-OL

生成物 1

HCID 202605943-(6-Chlorohexyl)quinoline収率 98.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

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. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 1 hour
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in dichloromethane
  5. washwashed successively with water, saturated sodium bicarbonate solution and brine
  6. dry with materialdried over potassium carbonate
  7. customevaporated

出典と根拠

ORDレコード
ord-376d3aa02fd445a492111439cd662d09
出典データセット
uspto-grants-1985_11
特許番号
US04551460

反応ノート

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