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

HRID 907939Notes

Reaction equation

HRID 907939 reaction equation
[CH:1]([C:3]1[CH:13]=[CH:12][C:6]([C:7]([N:9]([CH3:11])[CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.[CH2:14]([O:16][CH:17]([O:36][CH2:37][CH3:38])[C:18]1[CH:35]=[CH:34][C:21](/[CH:22]=[N:23]/[C:24]2[CH:32]=[CH:31][CH:30]=[C:29]3[C:25]=2[CH2:26][O:27][C:28]3=[O:33])=[CH:20][CH:19]=1)[CH3:15].[CH3:39][O-].[Na+].[C:42](OCC)(=[O:45])CC>>[CH2:14]([O:16][CH:17]([O:36][CH2:37][CH3:38])[C:18]1[CH:19]=[CH:20][C:21]([CH:22]2[CH:1]([C:3]3[CH:13]=[CH:12][C:6]([C:7](=[O:8])[N:9]([CH3:11])[CH3:10])=[CH:5][CH:4]=3)[C:42](=[O:45])[C:25]3[C:29]([C:28]([O:27][CH2:26][CH3:39])=[O:33])=[CH:30][CH:31]=[CH:32][C:24]=3[NH:23]2)=[CH:34][CH:35]=1)[CH3:15]

Participants

5

Reactant 4

HCID 7749Ethyl PropionateHCID 105592054-formyl-N,N-dimethylbenzamideHCID 10942334Sodium MethoxideHCID 178470922HCID 178470922, compound

Product 1

HCID 67258167Ethyl 2-(4-(diethoxymethyl)phenyl)-3-(4-(dimethylcarbamoyl)phenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

Procedure

To a mixture of 4-formyl-N,N-dimethylbenzamide (960 mg, 5.42 mmol), (E)-4-(4-(diethoxymethyl)benzylideneamino) isobenzofuran-1(3H)-one (1.84 g, 5.42 mmol) and sodium methoxide (499 mg, 21.7 mmol) was added to ethyl propionate (30 mL) and the mixture was stirred at room temperature overnight. Then the resulting mixture was evaporated under reduced pressure and extracted with EtOAc (100 mL×4) and concentrated. This gave the crude product (250 mg). LC-MS (ESI) m/z: 545 (M+1)+.

Workup

  1. customThen the resulting mixture was evaporated under reduced pressure
  2. extractionextracted with EtOAc (100 mL×4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0086eb34edb94fe0bb55d63397f1d365
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

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