Water → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-3-(4-methoxyphenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 1968121Notes

Reaction equation

HRID 1968121 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.[CH3:11][N:12]([CH2:14][C:15]1[CH:32]=[CH:31][C:18](/[CH:19]=[N:20]/[C:21]2[CH:29]=[CH:28]C=C3[C:22]=2[CH2:23][O:24]C3=O)=[CH:17][CH:16]=1)[CH3:13].C[O-].[Na+].O.[C:37]([O:41][CH2:42][CH3:43])(=[O:40])[CH2:38][CH3:39]>>[CH3:11][N:12]([CH2:14][C:15]1[CH:32]=[CH:31][C:18]([CH:19]2[CH:7]([C:6]3[CH:9]=[CH:10][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[C:23](=[O:24])[C:22]3[C:38]([C:37]([O:41][CH2:42][CH3:43])=[O:40])=[CH:39][CH:28]=[CH:29][C:21]=3[NH:20]2)=[CH:17][CH:16]=1)[CH3:13]

Participants

6

Reactant 5

HCID 962WaterHCID 7749Ethyl PropionateHCID 312444-MethoxybenzaldehydeHCID 10942334Sodium MethoxideHCID 178483208HCID 178483208, compound

Product 1

HCID 67259041Ethyl 2-(4-((dimethylamino)methyl)phenyl)-3-(4-methoxyphenyl)-4-oxo-1,2,3,4-tetrahydroquinoline-5-carboxylate

Conditions

Temperature
25 °C

Procedure

To a solution of 4-methoxybenzaldehyde (231 mg, 1.7 mmol) and (E)-4-(4-((dimethylamino)methyl)benzylideneamino)isobenzofuran-1(3H)-one (500 mg, 1.7 mmol) in ethyl propionate (30 mL) was added sodium methanolate (120 mg, 5.2 mmol) and the mixture was stirred at 25° C. for 4 h. Then the resulting mixture was added water (10 mL) and evaporated under reduced pressure, extracted with EtOAc (4×100 ml), and concentrated to dryness. A crude product was obtained (250 mg) and was used for next step reaction without further purification. LC-MS (ESI) m/z: 459 (M+1)+.

Workup

  1. customevaporated under reduced pressure
  2. extractionextracted with EtOAc (4×100 ml)
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-cb1b0037ae7642d9a5ea84967f7b507f
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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