5-Amino-2-methylphenol → 6-Fluoro4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrile

HRID 276862

Reaktionsgleichung

Reaktionsgleichung von HRID 276862
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].[OH:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][C:22]=1[CH3:23])[NH2:19].C(=O)(O)[O-].[Na+]>C(O)C.[Cl-].[Na+].O>[F:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][N:8]=1)[N:5]=[CH:4][C:3]([C:13]#[N:14])=[C:2]2[NH:19][C:18]1[CH:20]=[CH:21][C:22]([CH3:23])=[C:16]([OH:15])[CH:17]=1

Komponenten

6

Edukt 3

HCID 178185-Amino-2-methylphenolHCID 516892Sodium BicarbonateHCID 185489604-Chloro-6-fluoro-1,7-naphthyridine-3-carbonitrile

Produkt 1

HCID 185489376-Fluoro4-(3-hydroxy-4-methyl-phenylamino)-[1,7]naphthyridine-3-carbonitrileAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To 1.5 g of 4-chloro-6-fluoro-[1.7]naphthyridine-3-carbonitrile in 40 mL of absolute ethanol was added 1.1 g of 3-hydroxy-4-methylaniline. After stirring the reaction under an inert atmosphere for 16 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/ether/hexanes. Drying in vacuo yielded 1.9 g (90%) of 6-fluoro-4-(3-hydroxy-4-methyl-phenylamino)-[1.7]naphthyridine-3-carbonitrile as a yellow powder: melting point 236-239° C. (decomposed); mass spectrum (m/e): M+H 294.9.

Aufarbeitung

  1. customthe reaction under an inert atmosphere for 16 hours
  2. filtrationthe resultant crystals were filtered
  3. washwashed with water
  4. customThe product was then recrystallized from chloroform/ether/hexanes
  5. customDrying in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-77c528527e894238a8e296b6926c0c83
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355636B1

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