Ethyl Acrylate → 8-(2-ethoxycarbonyl-vinyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylate

HRID 1969989Notes

Reaction equation

HRID 1969989 reaction equation
I[C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3[NH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[CH:3]=1.[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17].[C:21]([O:25][CH2:26][CH3:27])(=[O:24])[CH:22]=[CH2:23]>>[CH2:26]([O:25][C:21]([CH:22]=[CH:23][C:2]1[CH:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C:6]3[NH:13][CH:14]=[CH:15][C:5]=3[C:4]=2[CH:3]=1)=[O:24])[CH3:27].[CH2:16]([C:18]([O-:20])=[O:19])[CH3:17]

Participants

3

Reactant 2

HCID 8821Ethyl AcrylateHCID 86627515HCID 86627515, compound

Product 1

HCID 866275148-(2-ethoxycarbonyl-vinyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline 1-ethyl carboxylateYield 22%

Procedure

This compound is prepared according to synthesis 68, from 114 mg (0.3 mmol) of 8-iodo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate and 36 μL (0.33 mmol) of ethyl acrylate. After purification by chromatography on silica (eluent dichloromethane/methanol 98/2) then trituration in ethanol, 23 mg (22%) of 8-(2-ethoxycarbonyl-vinyl)-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate is obtained in the form of a white solid.

Workup

  1. customThis compound is prepared
  2. customAfter purification by chromatography on silica (eluent dichloromethane/methanol 98/2)

Sources & evidence

ORD record
ord-ba95b8e4546d478aa035931c8fdb5676
Source dataset
uspto-grants-2013_04
Patent number
US08426437B2

Reaction notes

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