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

HRID 1967983Notes

Reaction equation

HRID 1967983 reaction equation
[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:8]=O)[CH3:2].[CH:10](=[N:17]/[C:18]1[CH:26]=[CH:25][CH:24]=[C:23]2[C:19]=1[CH2:20][O:21][C:22]2=[O:27])\[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH3:28][O-:29].[Na+].C(OCC)(=O)CC>>[CH2:1]([N:3]1[CH:7]=[CH:6][N:5]=[C:4]1[CH:8]1[C:28](=[O:29])[C:19]2[C:23]([C:22]([O:21][CH3:20])=[O:27])=[CH:24][CH:25]=[CH:26][C:18]=2[NH:17][CH:10]1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH3:2]

Participants

5

Reactant 4

HCID 7749Ethyl PropionateHCID 10942334Sodium MethoxideHCID 110623771-ethyl-1H-imidazole-2-carbaldehydeHCID 178519069HCID 178519069, compound

Product 1

HCID 67260994methyl 3-(1-ethyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 12.1%

Procedure

To 1-ethyl-1H-imidazole-2-carbaldehyde (520 mg, 4.19 mmol), (E)-4-(benzylideneamino) isobenzofuran-1(3H)-one (994 mg, 4.19 mmol), sodium methanolate (385 mg, 16.8 mmol) and ethyl propionate (15 mL) were added and the mixture was stirred at room temperature overnight. 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 5:1). 190 mg of methyl 3-(1-ethyl-1H-imidazol-2-yl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate was obtained. LC-MS (ESI) m/z: 390 (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 5:1)

Sources & evidence

ORD record
ord-e5bfe60074bb4078b08dcce90e412d18
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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