Ethyl 3-cyclopropyl-3-oxopropanoate → HCID 86682929, Verbindung

HRID 1497051Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1497051
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[Cl:17])[CH:3]=1.[CH:18]1([C:21](=O)[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:20][CH2:19]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>CCO>[CH2:26]([O:25][C:23]([C:22]1[C:21]([CH:18]2[CH2:20][CH2:19]2)=[N:8][C:5]2[C:4]([C:9]=1[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[Cl:17])=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[O:24])[CH3:27]

Komponenten

5

Edukt 3

HCID 262979Ethyl 3-cyclopropyl-3-oxopropanoateHCID 521998p-Toluenesulfonic acid monohydrateHCID 86682928HCID 86682928, Verbindung

Produkt 1

HCID 86682929HCID 86682929, VerbindungAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-2-(2-chloro-phenylethynyl)-phenylamine (100 mg, 0.38 mmol, 1 eq) and ethyl 3-cyclopropyl-3-oxopropanoate (89.4 mg, 0.57 mmol, 1.5 eq) in anhydrous EtOH (5 ml), was added p-TsOH.H2O (72.6 mg, 0.38 mmol, 1 eq) and the mixture was refluxed for 16 h. After cooling, the reaction mixture was concentrated in vacuo and then diluted with ethyl acetate. The mixture was washed with saturated sodium bicarbonate solution, brine, dried over sodium sulfate and concentrated in vacuo to give a crude residue which was purified by flash column chromatography (elution with 3% ethyl acetate in hexane) to give 6-chloro-4-(2-chloro-benzyl)-2-cyclopropyl-quinoline-3-carboxylic acid ethyl ester (33 mg, 22%) as a pale yellow solid. MS (ESI): 400.0 (M+H)+.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 16 h
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture was concentrated in vacuo
  4. additiondiluted with ethyl acetate
  5. washThe mixture was washed with saturated sodium bicarbonate solution, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give a crude residue which
  9. customwas purified by flash column chromatography (elution with 3% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-6fad11c4740a4507b2040faccafb0658
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09199938B2

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