Thionyl Chloride → 3-(6-Chlorohexyl)quinoline

HRID 1583434노트

반응식

HRID 1583434 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]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

참가 물질

4

반응물 2

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

생성물 1

HCID 202605943-(6-Chlorohexyl)quinoline수율 98.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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. 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

출처 및 근거

ORD 기록
ord-376d3aa02fd445a492111439cd662d09
출처 데이터셋
uspto-grants-1985_11
특허 번호
US04551460

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