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

HRID 351570

Reaction equation

HRID 351570 reaction equation
[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]

Participants

5

Reactant 2

HCID 5360315Magnesium Chloride2×HCID 20729419ethyl 3-(3,4-dihydroquinolin-1(2H)-yl)-2-oxopropanoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 80192-MethoxyethanolSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-059da2147817439cb31730d5e489abd0
Source dataset
uspto-grants-2004_06
Patent number
US06743785B2

Linked notes

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