Stannous Chloride → 5-Amino-2-hydroxy-2,4,6-cycloheptatrien-1-one

HRID 1689581

Reaktionsgleichung

Reaktionsgleichung von HRID 1689581
[CH:1]1[C:9](=[N:10]O)[CH:8]=[CH:7][C:5](=[O:6])[C:3](=[O:4])[CH:2]=1.[Sn](Cl)Cl>C(O)C>[CH:1]1[C:9]([NH2:10])=[CH:8][CH:7]=[C:5]([OH:6])[C:3](=[O:4])[CH:2]=1

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 178516264HCID 178516264, Verbindung

Produkt 1

HCID 234505-Amino-2-hydroxy-2,4,6-cycloheptatrien-1-oneAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a stirred solution of 0.39 g of 5-nitrosotropolone (2.6 mmole, obtained from the previous example) and 10 mL of absolute ethanol was added 2.92 g of Tin (II) chloride (12.9 mmole). After 40 minutes at reflux the solution was cooled, filtered, and the liquefied portion was partitioned between ethyl acetate and water. The organic fraction was concentrated in vacuo to give 35 mg (10%) of 5-aminotropolone as a yellow solid. IR spectroscopy of the product (neat) found the following characteristic IR absorption frequencies: 3319 cm−1, 3181 cm−1, 2925 cm−1, 1511 cm−1, 1410 cm−1, 1261 cm−1, 837 cm−1, 781 cm−1, and 739 cm−1.

Aufarbeitung

  1. temperatureAfter 40 minutes at reflux the solution
  2. temperaturewas cooled
  3. filtrationfiltered
  4. customthe liquefied portion was partitioned between ethyl acetate and water
  5. concentrationThe organic fraction was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-945129e1f28c4efdaf453b584afba424
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08153440B2

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