Potassium Carbonate → 5-Amino-2,2-dimethyl-2H-chromene-8-carbonitrile

HRID 751042Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751042
[CH3:1][C:2]1([CH3:17])[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([C:15]#[N:16])[CH:6]=[CH:7][C:8]=2[N+:12]([O-])=O)[O:3]1.Cl[Sn]Cl.C([O-])([O-])=O.[K+].[K+]>CCOC(C)=O>[NH2:12][C:8]1[CH:7]=[CH:6][C:5]([C:15]#[N:16])=[C:4]2[C:9]=1[CH:10]=[CH:11][C:2]([CH3:17])([CH3:1])[O:3]2

Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate2×HCID 24479Stannous ChlorideHCID 597542382,2-Dimethyl-5-nitro-2H-chromene-8-carbonitrile

Produkt 1

HCID 597542965-Amino-2,2-dimethyl-2H-chromene-8-carbonitrileAusbeute 79,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of compound 6B (230 mg, 1 mmol) in EtOAc (5 mL) was added SnCl2 2H2O (780 mg, 3.5 mmol). The resulting mixture was stirred at rt for 20 h, then saturated aqueous K2CO3 was added. After stirring for 30 min, the reaction was treated with solid K2CO3 (550 mg). The resulting suspension was stirred at rt for another 2 h, and then filtered. The filtrate was concentrated under reduced pressure to give a crude product, which was chromatographed (silica gel) eluting with 20% to 60% EtOAc/hexane to afford the title compound (160 mg) as a light yellow oil.

Aufarbeitung

  1. stirringAfter stirring for 30 min
  2. stirringThe resulting suspension was stirred at rt for another 2 h
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customto give a crude product, which
  6. customwas chromatographed (silica gel)
  7. washeluting with 20% to 60% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-d92b0ee73e6744f59a9a25a9f05f0ddc
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405234B2

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