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

HRID 1467651Notes

Reaction equation

HRID 1467651 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.[CH3:24][N:25]1[CH:29]=[CH:28][N:27]=[C:26]1[CH:30]=O.[Na].[CH2:33]([OH:35])[CH3:34]>C(OCC)(=O)CC>[CH3:23][N:2]([CH3:1])[C:3]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH:30]([C:26]3[N:25]([CH3:24])[CH:29]=[CH:28][N:27]=3)[C:14](=[O:15])[C:13]3[C:17]([C:16]([O:35][CH2:33][CH3:34])=[O:21])=[CH:18][CH:19]=[CH:20][C:12]=3[NH:11]2)=[CH:6][CH:5]=1)=[O:22]

Participants

6

Reactant 4

HCID 702EthanolHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 5360545SodiumHCID 178484438HCID 178484438, compound

Product 1

HCID 67261992Ethyl 2-(4-(dimethylcarbamoyl)phenyl)-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 37%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Procedure

(E)-N,N-Dimethyl-4-((1-oxo-1,3-dihydroisobenzofuran-4-ylimino)methyl)benzamide (924 mg, 3.0 mmol), 1-methyl-1H-imidazole-2-carbaldehyde (363 mg, 3.3 mmol), sodium (276 mg, 12 mmol) in ethanol (30 mL) and ethyl propionate (45 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 1:2) to afford the title compound as a yellow solid (500 mg, yield 37%). LC-MS (ESI) m/z: 447 (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 1:2)

Sources & evidence

ORD record
ord-e1797c4488a44dcaa10f60f7c355f826
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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