3-Chloropropionic acid → 3-(5-Quinolinoxy)-propionic acid

HRID 47058

반응식

HRID 47058 반응식
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.Cl[CH2:13][CH2:14][C:15]([OH:17])=[O:16]>[OH-].[K+]>[N:7]1[C:8]2[CH:9]=[CH:10][CH:11]=[C:2]([O:1][CH2:13][CH2:14][C:15]([OH:17])=[O:16])[C:3]=2[CH:4]=[CH:5][CH:6]=1

참가 물질

4

반응물 2

HCID 78993-Chloropropionic acidHCID 135441757Quinolin-5-ol

생성물 1

HCID 203850343-(5-Quinolinoxy)-propionic acid

시약·촉매·용매 1

HCID 14797Potassium Hydroxide용매3회

실험 절차

A solution of 5-hydroxyquinoline (4.91 g, 0.0340 mole) (Aldrich) in 17 ml 2 N potassium hydroxide was refluxed while an ice cold solution of 3-chloropropionic acid (4.05 g, 0.0373 mole) (Aldrich) in 18.6 ml 2 N potassium hydroxide was added during 1 minute. The pH was maintained at pH 9.5 by addition of 2 N potassium hydroxide. After 10 minutes, the mixture was allowed to come to room temperature and stirred for 16 hours. The pH of the solution was adjusted to pH 3.8 and the mixture evaporated in vacuo to a residue which was column chromatographed on silica gel by elution with 4:1 ethyl acetate:methanol. Material of Rf =0.45 (thin layer chromatography using 1:1 ethyl acetate:methanol) was obtained and recrystallized from water; m.p. 217°-219° C.

후처리

  1. additionwas added during 1 minute
  2. customto come to room temperature
  3. customthe mixture evaporated in vacuo to a residue which
  4. customchromatographed on silica gel by elution with 4:1 ethyl acetate
  5. customMaterial of Rf =0.45 (thin layer chromatography using 1:1 ethyl acetate:methanol) was obtained
  6. customrecrystallized from water

출처 및 근거

ORD 기록
ord-66f3661c35384156af4785ba593c9265
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04176185

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