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

HRID 1467758Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1467758
[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].[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][C:28]([CH:29]=O)=[CH:27][CH:26]=1.[O-:35][CH2:36][CH3:37].[Na+].CO>C(OCC)(=O)CC>[CH3:3][N:2]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]([CH:9]2[CH:29]([C:28]3[CH:31]=[CH:32][C:25]([C:24]([F:34])([F:33])[F:23])=[CH:26][CH:27]=3)[C:13](=[O:14])[C:12]3[C:16]([C:15]([O:35][CH2:36][CH3:37])=[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 887MethanolHCID 679964-(Trifluoromethyl)benzaldehydeHCID 2723922Sodium ethoxideHCID 178483208HCID 178483208, Verbindung

Produkt 1

HCID 67386466Ethyl 2-(4-((dimethylamino)methyl)phenyl)-4-oxo-3-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroquinoline-5-carboxylateAusbeute 16 %

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 (541 mg, 1.84 mmol) and 4-(trifluoromethyl)benzaldehyde (320 mg, 1.84 mmol) in anhydrous ethyl propionate (25 mL) was cooled to 0° C. Then sodium ethoxide in methanol solution (sodium (127 mg, 5.51 mmol) in anhydrous ethanol (10 mL)) was added dropwise and the mixture was stirred at 25° C. for 4 hr. The resulting mixture was quenched with water (5 mL), and then evaporated the solvents off under reduced pressure. The residue was extracted with ethyl acetate (100 mL×3) and the combined organic layers were dried over anhydrous sodium sulfate and concentrated to give crude product, which was purified by column chromatography (silica gel, dichloromethane to dichloromethane/methanol=30:1) to give the title compound (150 mg, yield 16%) as a yellow solid. LC-MS (ESI) m/z: 497 (M+1)+.

Aufarbeitung

  1. customThe resulting mixture was quenched with water (5 mL)
  2. customevaporated the solvents off under reduced pressure
  3. extractionThe residue was extracted with ethyl acetate (100 mL×3)
  4. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by column chromatography (silica gel, dichloromethane to dichloromethane/methanol=30:1)

Quellen und Nachweise

ORD-Eintrag
ord-dd4f76cba1ef4575bc5afa1ea728c5bf
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US08999987B2

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