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Acetic Acid → 7-tetrazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

HRID 1098304
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1098304
C(OC)(OC)OC.[N-:8]=[N+:9]=[N-:10].[Na+].[C:12](O)(=O)C.[NH2:16][C:17]1[CH:26]=[C:25]2[C:20]([CH:21]=[C:22]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[C:34]([F:37])([F:36])[F:35])[NH:23][C:24]2=[O:27])=[CH:19][CH:18]=1>O>[N:16]1([C:17]2[CH:26]=[C:25]3[C:20]([CH:21]=[C:22]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=4[C:34]([F:37])([F:35])[F:36])[NH:23][C:24]3=[O:27])=[CH:19][CH:18]=2)[CH:12]=[N:10][N:9]=[N:8]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 9005Trimethyl orthoformateHCID 33557Sodium AzideHCID 231567387-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one

Produkt 1

HCID 231567507-tetrazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-oneAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962
Water
Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

17.5 μl (0.16 mmol) of trimethyl orthoformate and 9.8 mg (0.15 mmol) of sodium azide were added to 0.2 ml of an acetic acid solution containing the 7-amino-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one obtained in Example 38. The obtained mixture was stirred at 80° C. for 6 hours. Thereafter, the reaction solution was cooled to a room temperature, and water was then added to thereto, followed by extraction with ethyl acetate. The extract was washed with a saturated sodium bicarbonate aqueous solution, and was then dried over anhydrous sodium sulfate, followed by concentration. The obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1), so as to obtain 29.8 mg (83%) of 7-tetrazol-1-yl-3-(2-trifluoromethylphenyl)-2H-isoquinolin-1-one in the form of a colorless solid.

Aufarbeitung

  1. temperatureThereafter, the reaction solution was cooled to a room temperature
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe extract was washed with a saturated sodium bicarbonate aqueous solution
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationfollowed by concentration
  6. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate:hexane=2:1)

Quellen und Nachweise

ORD-Eintrag
ord-43eefd375f8e43ee8c9df84003f3c8ec
Quelldatensatz
uspto-grants-2012_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08143274B2

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