Water → HCID 77385832, compound

HRID 1844836Notes

Reaction equation

HRID 1844836 reaction equation
[O:1]=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[N:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]1=2.N1[CH2:20][CH2:19][CH2:18][CH2:17]1.O.C(O[CH2:26][CH3:27])(=O)C>CO>[CH:26]1([CH:27]=[C:11]2[CH2:10][CH2:9][C:8]3[N:7]=[C:6]([C:12]([O:14][CH3:15])=[O:13])[CH:5]=[CH:4][C:3]=3[C:2]2=[O:1])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 31268PyrrolidineHCID 68010263HCID 68010263, compound

Product 1

HCID 77385832HCID 77385832, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a dried reaction flask, methyl 5-oxo-5,6,7,8-tetrahydroquinoline-2-carboxylate (1.97 g, 9.6 mmol), cyclopentylcarbaldehyde (2.05 mL, 19.20 mmol), and pyrrolidine (1.6 mL, 19.39 mmol) were dissolved in methanol (19 mL) at room temperature. In the protection from light and under the nitrogen atmosphere, the mixture was stirred at room temperature for 6 hr. To the mixture were added water and ethyl acetate. The mixture was extracted with ethyl acetate. The combined organic phase was washed with saturated salt water, dried over anhydrous sodium sulfate and purified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10) to obtain a pale yellow solid (1.589 g) in 58.0% yield.

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe combined organic phase was washed with saturated salt water
  3. dry with materialdried over anhydrous sodium sulfate
  4. custompurified by silica gel column chromatography (ethyl acetate:petroleum ether=1:10)

Sources & evidence

ORD record
ord-ad649923d7564376b7ce6b4edc070319
Source dataset
uspto-grants-2015_02
Patent number
US08946279B2

Reaction notes

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