Benzaldehyde → Ethyl 2-(4-((dimethylamino)methyl)phenyl)-7-fluoro-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylate

HRID 907983Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 907983
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:9][N:10]([CH2:12][C:13]1[CH:31]=[CH:30][C:16](/[CH:17]=[N:18]/[C:19]2[CH:27]=[C:26]([F:28])[CH:25]=[C:24]3[C:20]=2[CH2:21][O:22][C:23]3=[O:29])=[CH:15][CH:14]=1)[CH3:11].[O-:32][CH2:33][CH3:34].[Na+].C(O)C>C(OCC)(=O)CC>[CH3:9][N:10]([CH2:12][C:13]1[CH:31]=[CH:30][C:16]([CH:17]2[CH:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[C:33](=[O:32])[C:34]3[C:24]([C:23]([O:22][CH2:21][CH3:20])=[O:29])=[CH:25][C:26]([F:28])=[CH:27][C:19]=3[NH:18]2)=[CH:15][CH:14]=1)[CH3:11]

Komponenten

6

Edukt 4

HCID 240BenzaldehydeHCID 702EthanolHCID 2723922Sodium ethoxideHCID 178483209HCID 178483209, Verbindung

Produkt 1

HCID 67260728Ethyl 2-(4-((dimethylamino)methyl)phenyl)-7-fluoro-4-oxo-3-phenyl-1,2,3,4-tetrahydroquinoline-5-carboxylateAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7749Ethyl PropionateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of compound benzaldehyde (75 mg, 0.705 mmol) and (E)-4-(4-((dimethylamino)methyl)benzylideneamino)-6-fluoroisobenzofuran-1(3H)-one (220 mg, 0.705 mmol) in ethyl propionate (5 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (65 mg, 2.82 mmol) in ethanol (3 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 2.5 hr. The mixture was quenched with water (20 mL) and solvent was removed in vacuum. The residue was dissolved in water and extracted with ethyl acetate for three times. The extract was washed with water and brine and then the solvent was evaporated. The crude product was purified by chromatography to obtain the title compound as a yellow solid (80 mg, yield 25%). LC-MS (ESI) m/z: 447 (M+1)+.

Aufarbeitung

  1. additionAfter the addition
  2. customThe mixture was quenched with water (20 mL) and solvent
  3. customwas removed in vacuum
  4. dissolutionThe residue was dissolved in water
  5. extractionextracted with ethyl acetate for three times
  6. washThe extract was washed with water and brine
  7. customthe solvent was evaporated
  8. customThe crude product was purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e2ad5bd209d748cb9dab2e42b4089928
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08012976B2

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