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

HRID 1467677Notes

Reaction equation

HRID 1467677 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-d86abb3c26714f1db8968f1d3a4a2c1c
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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