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Acetonitrile → 1-(5-Carboxy-pentyl)-4-methyl-quinolinium iodide

HRID 252795
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HRID 252795 반응식
[N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1.C(#N)C.[I:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22]>CCOCC>[I-:15].[C:21]([CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N+:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]([CH3:5])=[CH:3][CH:2]=1)([OH:23])=[O:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 6342AcetonitrileHCID 102854-MethylquinolineHCID 128279486-Iodohexanoic acid

생성물 1

HCID 672626521-(5-Carboxy-pentyl)-4-methyl-quinolinium iodide수율 87.2%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a 250 mL flask were added lepidine (7.5 g, 52.4 mmol), acetonitrile (40 mL) and 6-iodohexanoic acid (14.0 g, 57.9 mmol). The mixture was heated at reflux under argon for 40 h and then was cooled to rt. The mixture was poured into stirred ether (700 mL) and the stirring was continued until the supernatant liquid was clear. The supernatant was decanted and the residue was dissolved in DCM (60 mL). The solution was poured slowly into stirred ether (700 mL). The initially formed oil solidified after stirring for approx. 3 h. The solid was crushed to a powder and stirring was continued for 1 h. The solid was filtered off, washed with ether (2×60 mL), and dried under vacuum to afford 14 as a tan colored solid (17.6 g, 87%).

후처리

  1. temperatureThe mixture was heated
  2. temperatureat reflux under argon for 40 h
  3. additionThe mixture was poured
  4. customThe supernatant was decanted
  5. dissolutionthe residue was dissolved in DCM (60 mL)
  6. additionThe solution was poured slowly
  7. stirringafter stirring for approx. 3 h
  8. customThe solid was crushed to a powder
  9. stirringstirring
  10. filtrationThe solid was filtered off
  11. washwashed with ether (2×60 mL)
  12. customdried under vacuum

출처 및 근거

ORD 기록
ord-fea76d1dfc46449785e809107deed035
출처 데이터셋
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07868157B2

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