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1-Phenyl-1,2-propanedione → HCID 23570722, Verbindung

HRID 1270817
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1270817
[C:1]([O:5][C:6]([N:8]1[CH:17]([CH:18]=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:20]1([C:26](=O)[C:27](=O)[CH3:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C([O-])(=O)C.[NH4+:35].[NH4+:36].[OH-]>CC(O)=O>[C:1]([O:5][C:6]([N:8]1[CH:17]([C:18]2[NH:35][C:27]([CH3:28])=[C:26]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)[N:36]=2)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 113631-Phenyl-1,2-propanedioneHCID 14923Ammonium HydroxideHCID 517165Ammonium AcetateHCID 12190329Tert-butyl 3-formyl-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Produkt 1

HCID 23570722HCID 23570722, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176
Acetic Acid
Lösungsmittel

Versuchsvorschrift

3-Formyl-3,4-dihydro-1H-isoquinoline-2-carboxylic acid tert-butyl ester (1.83 g, 7 mmol) was combined with AcOH (25 mL) to which was immediately added 1-phenyl-propane-1,2-dione (3.11 g, 21 mmol) and NH4OAc (13.49 g, 175 mmol). The reaction mixture was then placed on a steam bath and heated under an argon atmosphere for 20 minutes. The reaction mixture was cooled in an ice bath and then added to an ice slurry (44 g). The resulting mixture was basified by addition of concentrated NH4OH (50 mL) and then extracted twice with diethyl ether (150 mL each). The combined organic phases were dried over MgSO4, filtered and concentrated to yield crude product. This material was purified by preparative HPLC to yield the title compound as a white solid.

Aufarbeitung

  1. customThe reaction mixture was then placed on a steam bath
  2. temperatureheated under an argon atmosphere for 20 minutes
  3. temperatureThe reaction mixture was cooled in an ice bath
  4. extractionextracted twice with diethyl ether (150 mL each)
  5. dry with materialThe combined organic phases were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto yield crude product
  9. customThis material was purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-9ee745e6d378488eabf7e15e5a6d13af
Quelldatensatz
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07202381B2

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