Potassium Carbonate → 7-bromo-N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamine

HRID 909352

Reaktionsgleichung

Reaktionsgleichung von HRID 909352
S(S([O-])=O)([O-])=O.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[Br:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[C:21]([N+:26]([O-])=O)[CH:22]=[N:23]2)=[N:18][CH:17]=1>O.ClCCl.CC[N+]1C=CC(C2C=C[N+](CC)=CC=2)=CC=1.[Br-].[Br-]>[Br:15][C:16]1[CH:25]=[C:24]2[C:19]([C:20]([NH:29][CH2:30][CH:31]([CH3:33])[CH3:32])=[C:21]([NH2:26])[CH:22]=[N:23]2)=[N:18][CH:17]=1

Komponenten

7

Edukt 3

HCID 11430Potassium CarbonateHCID 24489Sodium DithioniteHCID 670522117-bromo-N-(2-methylpropyl)-3-nitro[1,5]naphthyridin-4-amine

Produkt 1

HCID 688188847-bromo-N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamineAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 114742621,1'-Diethyl-4,4'-bipyridinium dibromideKatalysatorHCID 962WaterLösungsmittel3×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of sodium dithionite (77.95 g, 380.6 mmol) and potassium carbonate (58.35 g, 422.2 mmol) in water (250 mL) was added dropwise to a mechanically stirred solution of 7-bromo-3-nitro[1,5]naphthyridin-4-yl-(2-methylpropyl)amine (27.6 g, 84.6 mmol) and ethyl viologen dibromide (0.63 g, 1.7 mmol) in dichloromethane (300 mL) and water (50 mL). The reaction mixture was stirred overnight at ambient temperature. Water (500 mL) was added, and the reaction mixture was stirred for 10 minutes. The organic layer was separated and the aqueous layer was filtered through WHATMAN paper to remove insoluble material. The emulsion-free filtrate was extracted with dichloromethane, washed sequentially with water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to yield 22.3 g of 7-bromo-N4-(2-methylpropyl)[1,5]naphthyridine-3,4-diamine as an orange solid.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 10 minutes
  2. customThe organic layer was separated
  3. filtrationthe aqueous layer was filtered through WHATMAN paper
  4. customto remove insoluble material
  5. extractionThe emulsion-free filtrate was extracted with dichloromethane
  6. washwashed sequentially with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f7a0a0b2c0eb49a2b9f548cde87d3fc1
Quelldatensatz
uspto-grants-2011_09
Patentnummer
US08017779B2

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