Ethyl Propionate → HCID 67260881, compound

HRID 1467606Notes

Reaction equation

HRID 1467606 reaction equation
[CH2:1]([N:4]1[CH:8]=[CH:7][N:6]=[C:5]1[CH:9]=O)[CH2:2][CH3:3].[CH:11](=[N:18]/[C:19]1[CH:27]=[CH:26]C=C2[C:20]=1[CH2:21][O:22]C2=O)\[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C[O-].[Na+].[C:32]([O:36][CH2:37][CH3:38])(=[O:35])[CH2:33][CH3:34]>>[O:22]=[C:21]1[C:20]2[C:33]([C:32]([O:36][CH2:37][CH3:38])=[O:35])=[CH:34][CH:26]=[CH:27][C:19]=2[NH:18][CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]1[C:5]1[N:4]([CH2:1][CH2:2][CH3:3])[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 4

HCID 7749Ethyl PropionateHCID 47776601-Propyl-1H-imidazole-2-carbaldehydeHCID 10942334Sodium MethoxideHCID 178519069HCID 178519069, compound

Product 1

HCID 67260881HCID 67260881, compoundYield 30%

Procedure

To the mixture of 1-propyl-1H-imidazole-2-carbaldehyde (1.1 g, 8.0 mmol) and (E)-4-(benzylideneamino) isobenzofuran-1(3H)-one (1.7 g, 7.2 mmol) were added in ethyl propionate (50 mL) and then sodium methoxide was added under 0° C. The mixture was stirred overnight at room temperature. The mixture was concentrated and the residue was extracted with ethyl acetate (100 mL×4). The organic layer dried over anhydrous sodium sulfate, purified by chromatography (silica gel, petroleum ether/ethyl acetate=10:1 to 1:1) to give ethyl 4-oxo-2-phenyl-3-(1-propyl-1H-imidazol-2-yl)-1,2,3,4-tetrahydroquinoline-5-carboxylate (770 mg, yield 30%). LC-MS (ESI) m/z: 404 (M+1)+.

Workup

  1. concentrationThe mixture was concentrated
  2. extractionthe residue was extracted with ethyl acetate (100 mL×4)
  3. dry with materialThe organic layer dried over anhydrous sodium sulfate
  4. custompurified by chromatography (silica gel, petroleum ether/ethyl acetate=10:1 to 1:1)

Sources & evidence

ORD record
ord-834fcb10f3684269a4279fce0423a2e7
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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