2,4-Dichloroaniline → 4-(2,4-Dichloro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile

HRID 1266292Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1266292
Cl[C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14].[Cl:15][C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=1[NH2:18].C(=O)(O)[O-].[Na+]>CO.[Cl-].[Na+].O>[Cl:15][C:16]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:17]=1[NH:18][C:2]1[C:11]2[C:6](=[CH:7][N:8]=[C:9]([F:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[C:13]#[N:14]

Komponenten

6

Edukt 3

HCID 111232,4-DichloroanilineHCID 516892Sodium BicarbonateHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Produkt 1

HCID 185489484-(2,4-Dichloro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrileAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To 2.0 g of 4-chloro-6-fluoro-[1,7]naphthyridine-3-carbonitrile in 50 mL of methanol was added 1.9 g of 2,4-dichloroaniline. After refluxing the reaction under an inert atmosphere for 2 hours, the reaction mixture was poured into a mixture of brine and saturated aqueous sodium bicarbonate and the resultant crystals were filtered and washed with water. The product was then recrystallized from chloroform/hexanes. Drying in vacuo yielded 2.6 g (80%) of 4-(2,4dichloro-phenylamino)-6-fluoro-[1,7]naphthyridine-3-carbonitrile as yellow needles: melting point 206-208° C.; mass spectrum (m/e): M+H 332.8.

Aufarbeitung

  1. temperatureAfter refluxing
  2. customthe reaction under an inert atmosphere for 2 hours
  3. filtrationthe resultant crystals were filtered
  4. washwashed with water
  5. customThe product was then recrystallized from chloroform/hexanes
  6. customDrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-11201d1a5c444578a4fec74fc36c21ff
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06548496B2

Notizen zur Reaktion

Wird geladen…