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Ethanol → Ethyl 1,2,3,4-tetrahydro-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-2-[4-(trifluoromethyl)phenyl]-5-quinolinecarboxylate

HRID 907930
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 907930
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:20]=[CH:19][C:6](/[CH:7]=[N:8]/[C:9]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:10]=2[CH2:11][O:12][C:13]3=[O:18])=[CH:5][CH:4]=1.[CH3:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[CH:29]=O.[O-:31][CH2:32][CH3:33].[Na+].C(O)C>C(OCC)(=O)CC>[CH3:23][N:24]1[CH:28]=[CH:27][N:26]=[C:25]1[CH:29]1[C:11](=[O:12])[C:10]2[C:14]([C:13]([O:31][CH2:32][CH3:33])=[O:18])=[CH:15][CH:16]=[CH:17][C:9]=2[NH:8][CH:7]1[C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:20][CH:19]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 702EthanolHCID 1395751-Methyl-2-imidazolecarboxaldehydeHCID 2723922Sodium ethoxideHCID 178519072HCID 178519072, Verbindung

Produkt 1

HCID 67260485Ethyl 1,2,3,4-tetrahydro-3-(1-methyl-1H-imidazol-2-yl)-4-oxo-2-[4-(trifluoromethyl)phenyl]-5-quinolinecarboxylateAusbeute 8 %

Reagenzien, Katalysatoren, Lösungsmittel

1
HCID 7749Ethyl PropionateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A mixture of (E)-4-(4-(trifluoromethyl)benzylideneamino)isobenzofuran-1(3H)-one (1 g, 3.28 mmol) and N-methyl-2-imidazolecarbaldehyde (400 mg, 3.61 mmol) in ethyl propionate (40 mL) was cooled to 0° C. Then a solution of sodium ethoxide in ethanol (sodium (31 mg, 13.1 mmol) in ethanol (10 mL)) was added dropwise. After the addition, the mixture was stirred at room temperature for 2 hr. The mixture was quenched with water (10 mL) and solvent was removed in vacuum. The residue was dissolved in water, and then extracted with ethyl acetate (100 mL×4). 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 chromatography (silica gel, petroleum ether/ethyl acetate=1:1) to give the title compound (150 mg, yield 8%). LC-MS (ESI) m/z: 444 (M+1)+.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bd5648361b48417286b8c97937ae0b5b
Quelldatensatz
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08012976B2

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