Stannous chloride dihydrate → N4-(3-Ethynylphenyl)quinazoline-4,6-diamine

HRID 1968641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1968641
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2].O.O.Cl[Sn]Cl.C([O-])(O)=O.[Na+]>C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:6]=[CH:7][CH:8]=1)#[CH:2]

Komponenten

5

Edukt 3

HCID 61436Stannous chloride dihydrateHCID 516892Sodium BicarbonateHCID 16045443N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine

Produkt 1

HCID 11492625N4-(3-Ethynylphenyl)quinazoline-4,6-diamineAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

N-(3-ethynylphenyl)-6-nitroquinazolin-4-amine (1.00 g, 3.45 mmol) and SnCl2.2H2O (3.10 g, 13.8 mmol) in ethyl acetate (35 mL) were refluxed for 2 h. After cooled to room temperature, the mixture was treated with 5% aqueous NaHCO3 to adjust its pH to 9-10 and then subjected to extraction with EtOAc. The combined organic layers were washed with saturated brine and H2O, dried, and concentrated under reduced pressure to give 0.79 g (89%) of N4-(3-ethynylphenyl)quinazoline-4,6-diamine as a yellow solid.

Aufarbeitung

  1. extractionsubjected to extraction with EtOAc
  2. washThe combined organic layers were washed with saturated brine and H2O
  3. customdried
  4. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-2aae24fbcb9f43b9a6d1da031fd01484
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426430B2

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