N-(3-chloro-4-fluoro-phenyl)-7-(2-methoxyethoxy)-6-nitro-quinazolin-4-amine → N4-(3-Chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine

HRID 2199351Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2199351
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:17]([N+:20]([O-])=O)[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:23][CH2:24][CH2:25][O:26][CH3:27])=[C:17]([NH2:20])[CH:18]=3)[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

4

Edukt 1

HCID 18765556N-(3-chloro-4-fluoro-phenyl)-7-(2-methoxyethoxy)-6-nitro-quinazolin-4-amine

Produkt 1

HCID 18765584N4-(3-Chloro-4-fluorophenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamineAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

N-(3-Chloro-4-fluoro-phenyl)-7-(2-methoxyethoxy)-6-nitro-quinazolin-4-amine 8b (392 mg, 1 mmol) and iron powder (392 mg, 7 mmol) were dissolved in 20 mL of acetic acid. The reaction mixture was heated to reflux for 4 hours, concentrated under reduced pressure. The residue was added with 100 mL of saturated sodium bicarbonate, extracted with dichloromethane (100 mL×3). The combined organic extracts were washed with saturated brine (50 mL×2), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to obtain the title compound N4-(3-chloro-4-fluoro-phenyl)-7-(2-methoxyethoxy)quinazoline-4,6-diamine 8c (200 mg, yield 55.2%) as a light yellow solid.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 4 hours
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was added with 100 mL of saturated sodium bicarbonate
  5. extractionextracted with dichloromethane (100 mL×3)
  6. washThe combined organic extracts were washed with saturated brine (50 mL×2)
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-7fef96e5f1ca4f5a82d02757923be6a7
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09358227B2

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