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2-benzyl-6-bromo-3-(1-hydroxyethyl)-4-phenyl-2H-isoquinolin-1-one → 3-acetyl-2-benzyl-6-bromo-4-phenyl-2H-isoquinolin-1-one

HRID 750265
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 750265
[CH2:1]([N:8]1[C:17]([CH:18]([OH:20])[CH3:19])=[C:16]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Br:27])[CH:14]=2)[C:9]1=[O:28])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[O-2].[Mn+4].[O-2]>[C:18]([C:17]1[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:9](=[O:28])[C:10]2[C:15]([C:16]=1[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[CH:14][C:13]([Br:27])=[CH:12][CH:11]=2)(=[O:20])[CH3:19]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 1

HCID 230610042-benzyl-6-bromo-3-(1-hydroxyethyl)-4-phenyl-2H-isoquinolin-1-one

Produkt 1

HCID 230606723-acetyl-2-benzyl-6-bromo-4-phenyl-2H-isoquinolin-1-oneAusbeute 60,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysator4×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 2-benzyl-6-bromo-3-(1-hydroxyethyl)-4-phenyl-2H-isoquinolin-1-one (250 mg) in THF (5 ml) was added manganese(IV) oxide (500 mg), and the mixture was heated under reflux for 1 hr. To the reaction mixture was add manganese(IV) oxide (500 mg) and the mixture was heated under reflux for 1 hr, manganese(IV) oxide (500 mg) was added and the mixture was heated under reflux for 1 hr, and manganese(IV) oxide (500 mg) was added and the mixture was heated under reflux for 12 hrs. The reaction mixture was filtered and the filtrate was concentrated. The obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=8:1) and recrystallized (ethyl acetate-hexane) to give the title compound (150 mg).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux for 1 hr
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 1 hr
  7. temperaturethe mixture was heated
  8. temperatureunder reflux for 12 hrs
  9. filtrationThe reaction mixture was filtered
  10. concentrationthe filtrate was concentrated
  11. customThe obtained residue was purified by silica gel column chromatography (hexane-hexane:ethyl acetate=8:1)
  12. customrecrystallized (ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-d3ed62cbaa01469591e40e2ebb28bc3b
Quelldatensatz
uspto-grants-2008_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07402595B2

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