Ethanol → Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907937Notes

Reaction equation

HRID 907937 reaction equation
[CH3:1][N:2]([CH3:23])[C:3](=[O:22])[C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[N:11]/[C:12]2[CH:20]=[CH:19][CH:18]=[C:17]3[C:13]=2[CH2:14][O:15][C:16]3=[O:21])=[CH:6][CH:5]=1.[F:24][C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.[Na].[C:34](OCC)(=[O:37])CC.[CH2:41](O)C>>[CH3:1][N:2]([CH3:23])[C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH:29]([C:28]3[CH:31]=[CH:32][C:25]([F:24])=[CH:26][CH:27]=3)[C:34](=[O:37])[C:13]3[C:17]([C:16]([O:15][CH2:14][CH3:41])=[O:21])=[CH:18][CH:19]=[CH:20][C:12]=3[NH:11]2)=[CH:6][CH:5]=1)=[O:22]

Participants

6

Reactant 5

HCID 702EthanolHCID 7749Ethyl PropionateHCID 680234-FluorobenzaldehydeHCID 5360545SodiumHCID 178484438HCID 178484438, compound

Product 1

HCID 67261345Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(4-fluorophenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 22%

Procedure

Compound (E)-N,N-dimethyl-4-((1-oxo-1,3-dihydroisobenzofuran-4-ylimino)methyl)benzamide (1.36 g, 4.4 mmol), 4-fluorobenzaldehyde (600 mg, 4.84 mmol), sodium (405 mg, 17.6 mmol), ethanol (40 mL) and ethyl propionate (66 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) to give the title compound as a solid (490 mg, yield 22%). LC-MS (ESI) m/z: 461(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-2e1e625ecdcd4ceabad44ccffba642f8
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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