Magnesium Chloride → Ethyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylate

HRID 351570

반응식

HRID 351570 반응식
[Cl-].[Mg+2].[Cl-].[CH2:4]([O:6][C:7](=[O:21])[C:8](=O)[CH2:9][N:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13][CH2:12][CH2:11]1)[CH3:5]>COCCO.O1CCCC1>[CH2:4]([O:6][C:7]([C:8]1[C:18]2=[C:19]3[C:14](=[CH:15][CH:16]=[CH:17]2)[CH2:13][CH2:12][CH2:11][N:10]3[CH:9]=1)=[O:21])[CH3:5]

참가 물질

5

반응물 2

HCID 5360315Magnesium Chloride2회HCID 20729419ethyl 3-(3,4-dihydroquinolin-1(2H)-yl)-2-oxopropanoate

생성물 1

HCID 20729414Ethyl 5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinoline-1-carboxylate수율 48%

시약·촉매·용매 2

HCID 80192-Methoxyethanol용매2회HCID 8028Tetrahydrofuran용매

실험 절차

Magnesium chloride (27.7 g, 0.29 mol) was added to 2-methoxyethanol (400 mL) and the mixture heated to reflux. A solution of 3-(3,4-Dihydro-2H-quinolin-1-yl)-2-oxopropionic acid ethyl ester (0.29 mol) in 2-methoxyethanol (100 mL) and tetrahydrofuran (40 mL) was slowly added to the MgCl2 mixture over 1 hour. Upon completion of addition, the mixture was stirred for 5 hours at reflux, and then concentrated in vacuo. The concentrated crude mixture was treated with 2N hydrochloric acid (500 mL) and extracted with dichloromethane (3×400 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was subjected to silica gel chromatography, eluting with 20% ethyl acetate/hexanes. Fractions containing product were combined and concentrated under reduced pressure to provide 31.6 g (48%) of the desired compound as an orange solid.

후처리

  1. temperaturethe mixture heated to reflux
  2. additionUpon completion of addition
  3. temperatureat reflux
  4. concentrationconcentrated in vacuo
  5. concentrationThe concentrated crude mixture
  6. additionwas treated with 2N hydrochloric acid (500 mL)
  7. extractionextracted with dichloromethane (3×400 mL)
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. washeluting with 20% ethyl acetate/hexanes
  12. additionFractions containing product
  13. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-059da2147817439cb31730d5e489abd0
출처 데이터셋
uspto-grants-2004_06
특허 번호
US06743785B2

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