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

HRID 1467560Notes

Reaction equation

HRID 1467560 reaction equation
[CH3:1][O:2][CH:3]([O:22][CH3:23])[C:4]1[CH:21]=[CH:20][C:7](/[CH:8]=[N:9]/[C:10]2[CH:18]=[CH:17][CH:16]=[C:15]3[C:11]=2[CH2:12][O:13][C:14]3=[O:19])=[CH:6][CH:5]=1.[CH:24](=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.[CH3:32][O-:33].[Na+]>C(OCC)(=O)CC>[CH3:23][O:22][CH:3]([O:2][CH3:1])[C:4]1[CH:21]=[CH:20][C:7]([CH:8]2[CH:24]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:32](=[O:33])[C:11]3[C:15]([C:14]([O:13][CH3:12])=[O:19])=[CH:16][CH:17]=[CH:18][C:10]=3[NH:9]2)=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 10942334Sodium MethoxideHCID 178499418HCID 178499418, compound

Product 1

HCID 67260583Methyl 2-(4-(dimethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 27.8%

Reagents, catalysts & solvents 1

HCID 7749Ethyl PropionateSolvent

Procedure

To a solution of (E)-4-(4-(dimethoxymethyl)benzylideneamino)isobenzofuran-1(3H)-one (600 mg, 1 mmol) and benzaldehyde (616 mg, 3 mmol) in ethyl propionate (20 mL), sodium methanolate (414 mg, 7.6 mmol) 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 obtain a white solid of methyl 2-(4-(dimethoxymethyl)phenyl)-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (120 mg, yield 22%). LC-MS (ESI) m/z: 432 (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-28f7dee9ea6e42678015611378d01bbd
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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