Benzaldehyde → Methyl 2-(4-(dimethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1467521Notes

Reaction equation

HRID 1467521 reaction equation
[CH2:1]([O:3][CH:4]([O:23][CH2:24]C)[C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[CH:18][CH:17]=C3C=2COC3=O)=[CH:7][CH:6]=1)C.[CH:26](=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[CH3:34][O-:35].[Na+].[C:37]([O:41][CH2:42]C)(=[O:40])[CH2:38][CH3:39]>>[CH3:24][O:23][CH:4]([O:3][CH3:1])[C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[CH:26]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:34](=[O:35])[C:39]3[C:38]([C:37]([O:41][CH3:42])=[O:40])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:21][CH:22]=1

Participants

5

Reactant 4

HCID 240BenzaldehydeHCID 7749Ethyl PropionateHCID 10942334Sodium MethoxideHCID 178470922HCID 178470922, compound

Product 1

HCID 67260583Methyl 2-(4-(dimethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 22%

Procedure

(E)-4-(4-(diethoxymethyl)benzylideneamino)isobenzofuran-1(3H)-one (600 mg, 1 mmol), benzaldehyde (616 mg, 3 mmol), sodium methanolate (414 mg, 7.6 mmol) and ethyl propionate (20 ml) were added and the mixture was stirred at room temperature overnight. The resulting mixture was then 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 yield 120 mg of solid of methyl 2-(4-(dimethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (yield: 22%). LC-MS (ESI) m/z: 432 (M+1)+.

Workup

  1. customThe resulting mixture was then 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-b3239c53e3984cb39a14266ebd602b29
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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