Ethyl Propionate → ethyl 2-(4-(diethoxymethyl)phenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907843Notes

Reaction equation

HRID 907843 reaction equation
[CH2:1]([O:3][CH:4]([O:23][CH2:24][CH3:25])[C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][O:14][C:15]3=[O:20])=[CH:7][CH:6]=1)[CH3:2].[CH3:26][N:27]1[CH:31]=[CH:30][N:29]=[C:28]1[CH:32]=O.[CH2:34]([O-])[CH3:35].[Na+].C(OCC)(=[O:41])CC>>[CH2:1]([O:3][CH:4]([O:23][CH2:24][CH3:25])[C:5]1[CH:22]=[CH:21][C:8]([CH:9]2[CH:32]([C:28]3[N:27]([CH3:26])[CH:31]=[CH:30][N:29]=3)[C:13](=[O:41])[C:12]3[C:16]([C:15]([O:14][CH2:34][CH3:35])=[O:20])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

5

Reactant 4

HCID 7749Ethyl PropionateHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 2723922Sodium ethoxideHCID 178470922HCID 178470922, compound

Product 1

HCID 67260396ethyl 2-(4-(diethoxymethyl)phenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 5%

Procedure

A mixture of (E)-4-(4-(diethoxymethyl)benzylideneamino)isobenzofuran-1(3H)-one (678 mg, 2 mmol), 1-methyl-1H-imidazole-2-carbaldehyde (242 mg, 2.2 mmol), sodium ethanolate (544 mg, 8.0 mmol), and ethyl propionate (50 ml) was stirred at room temperature for 3 hr. Then the resulting mixture was evaporated under reduced pressure and extracted with ethyl acetate (100 mL×4) and concentrated. The crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1 to 1.5:1) to give ethyl 2-(4-(diethoxymethyl)phenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate as solid (50 mg, yield 5%). LC-MS (ESI) m/z: 478 (M+1)+.

Workup

  1. customThen the resulting mixture was evaporated under reduced pressure
  2. extractionextracted with ethyl acetate (100 mL×4)
  3. concentrationconcentrated
  4. customThe crude product was purified by column chromatography (silica gel, petroleum ether:ethyl acetate=20:1 to 1.5:1)

Sources & evidence

ORD record
ord-e8d14fa1fb024cb59f3cca49ed5ce7c3
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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