Methanol → Methyl 3-(3-(diethoxymethyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1967898Notes

Reaction equation

HRID 1967898 reaction equation
[CH:1](=[N:8]/[C:9]1C=CC=[C:14]2[C:10]=1CO[C:13]2=O)\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:19]([O:21][CH:22]([O:31][CH2:32][CH3:33])[C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O)[CH3:20].[CH3:34][O-:35].[Na+].CO.[C:39]([O:43][CH2:44]C)(=[O:42])[CH2:40][CH3:41]>>[CH2:19]([O:21][CH:22]([O:31][CH2:32][CH3:33])[C:23]1[CH:24]=[C:25]([CH:26]2[C:34](=[O:35])[C:41]3[C:40]([C:39]([O:43][CH3:44])=[O:42])=[CH:13][CH:14]=[CH:10][C:9]=3[NH:8][CH:1]2[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:28]=[CH:29][CH:30]=1)[CH3:20]

Participants

6

Reactant 5

HCID 887MethanolHCID 7749Ethyl PropionateHCID 10942334Sodium MethoxideHCID 162177103-(Diethoxymethyl)benzaldehydeHCID 178519069HCID 178519069, compound

Product 1

HCID 67261363Methyl 3-(3-(diethoxymethyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateYield 25%

Conditions

Temperature
0 °C

Procedure

A mixture of (E)-4-(benzylideneamino)isobenzofuran-1(3H)-one (474 mg, 2 mmol) and 3-(diethoxymethyl)benzaldehyde (418 mg, 2 mmol) in ethyl propionate (20 mL) was cooled to 0° C. Sodium methoxide in methanol solution [sodium (148 mg, 8 mmol) in methanol (2 mL)] was then added dropwise and the mixture was stirred at room temperature overnight. The resulting mixture was evaporated under reduced pressure. The residue was extracted with ethyl acetate (100 mL×3) and the combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated to give crude product. The crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=50:1 to 5:1) to give methyl 3-(3-(diethoxymethyl)phenyl)-4-oxo-2-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate (230 mg, yield 25%) as a yellow solid.

Workup

  1. customThe resulting mixture was evaporated under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate (100 mL×3)
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product
  7. customThe crude product was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=50:1 to 5:1)

Sources & evidence

ORD record
ord-fee06fae505142febe2dff34227d0ca2
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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