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Hydrochloric Acid → 6-Acetyl-4,4-dimethyl-3,4-dihydroquinolin-2(1h)-one

HRID 1840872
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1840872
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][C:5]2([CH3:14])[CH3:13].C([Sn](CCCC)(CCCC)[C:20]([O:22]CC)=[CH2:21])CCC.Cl>C1COCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:20]([C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][C:5]2([CH3:14])[CH3:13])(=[O:22])[CH3:21]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 107295896-bromo-4,4-dimethyl-3,4-dihydroquinolin-2(1H)-one2×

Produkt 1

HCID 234447026-Acetyl-4,4-dimethyl-3,4-dihydroquinolin-2(1h)-oneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476
HCID 178418476, Verbindung
Katalysator
HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A solution of 6-bromo-4,4-dimethyl-3,4-dihydro-1H-quinolin-2-one (Intermediate 4, 270 mg, 1.06 mmol) in 5 ml of THF was first degassed by bubbling with argon for 30 min. Tributyl(1-ethoxyvinyl)tin (766 mg, 2.12 mmol) and PdCl2(PPh3)2 (37mg, 0.05 mmol) were added. After stirring at 80° C. for 18 h, the mixture was cooled to room temperature and 3 mL of 10% HCl was added. The mixture was then stirred for another 30 min before extracted with ethyl acetate (3×10 mL). The combined organic layer was washed with brine (1×10 mL), dried (MgSO4) and concentrated at reduced pressure. Purification by flash chormatography (50:50 hexane/ethyl acetate) yielded the title compound as a white solid (154 mg, 67% yield).

Aufarbeitung

  1. customby bubbling with argon for 30 min
  2. temperaturethe mixture was cooled to room temperature
  3. stirringThe mixture was then stirred for another 30 min
  4. extractionbefore extracted with ethyl acetate (3×10 mL)
  5. washThe combined organic layer was washed with brine (1×10 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated at reduced pressure
  8. customPurification by flash chormatography (50:50 hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-2284227a08b34a7f97e9de14f83ae5b1
Quelldatensatz
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06683092B1

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