Ethanol → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-p-tolyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907999
[CH3:1][N:2]([CH2:4][C:5]1[CH:22]=[CH:21][C:8](/[CH:9]=[N:10]/[C:11]2[CH:19]=[CH:18][CH:17]=[C:16]3[C:12]=2[CH2:13][O:14][C:15]3=[O:20])=[CH:7][CH:6]=1)[CH3:3].[CH3:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1.[O-:32][CH2:33][CH3:34].[Na+].C(O)C>C(OCC)(=O)CC>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[CH:23]([C:24]3[CH:31]=[CH:30][C:27]([CH3:28])=[CH:26][CH:25]=3)[C:13](=[O:14])[C:12]3[C:16]([C:15]([O:32][CH2:33][CH3:34])=[O:20])=[CH:17][CH:18]=[CH:19][C:11]=3[NH:10]2)=[CH:21][CH:22]=1)[CH3:1]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 77254-MethylbenzaldehydeHCID 2723922Sodium ethoxideHCID 178483208HCID 178483208, Verbindung

Produkt 1

HCID 67259015Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-p-tolyl-1,2,3,4-tetrahydroquinoline-5-carboxylateAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7749Ethyl PropionateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of (E)-4-(4-((dimethylamino)methyl)benzylideneamino)isobenzofuran-1(3H)-one (500 mg, 1.7 mmol) and 4-methylbenzaldehyde (204 mg, 1.7 mmol) in ethyl propionate (30 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (156 mg, 6.8 mmol) in ethanol (30 mL)) was added dropwise. After the addition, the mixture was stirred at 10° C. for 1 hr, then at 30° C. for 3 hr. The mixture was quenched with water (30 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (30 mL×4). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, and concentrated to give crude product, which was purified by chromatography (silica gel, dichloromethane/methanol=100:1 to 10:1) to give the title compound (110 mg, yield: 15%). LC-MS (ESI) m/z: 443 (M+1)+.

Aufarbeitung

  1. additionAfter the addition
  2. waitat 30° C. for 3 hr
  3. customThe mixture was quenched with water (30 mL) and solvent
  4. customwas removed in vacuum
  5. dissolutionThe residue was dissolved in water
  6. extractionextracted with ethyl acetate (30 mL×4)
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated
  10. customto give crude product, which
  11. customwas purified by chromatography (silica gel, dichloromethane/methanol=100:1 to 10:1)

Quellen und Nachweise

ORD-Eintrag
ord-23a225ee02b945fb90bca7c433107345
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012976B2

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