Phosphorus oxychloride → 1,5-Naphthyridine-3-carbonitrile, 4-chloro-6-methyl-

HRID 968713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 968713
[CH3:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]([C:12]#[N:13])[C:5]2=O.O=P(Cl)(Cl)[Cl:17]>>[Cl:17][C:5]1[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([CH3:1])[N:3]=2)[N:8]=[CH:7][C:6]=1[C:12]#[N:13]

Komponenten

3

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 587242946-Methyl-4-oxo-1,4-dihydro-1,5-naphthyridine-3-carbonitrile

Produkt 1

HCID 587242971,5-Naphthyridine-3-carbonitrile, 4-chloro-6-methyl-Ausbeute 57,1 %

Versuchsvorschrift

The suspension of 6-methyl-4-oxo-1,4-dihydro-[1,5]naphthyridine-3-carbonitrile (1.47 g, 7.93 mmol) in POCl3 (25 mL) was heated under refluxing for 2 hrs. After cooling to room temperature, the reaction mixture was quenched with ice water and basified with NH4OH followed by extraction with AcOEt. The organic layer was washed with brine and dried over NaSO4, and concentrated to give 4-chloro-6-methyl-[1,5]naphthyridine-3-carbonitrile as a brown solid (0.92 g, 57.1%). HR-MS-EI (+) m/e calcd for C10H6ClN3 (M+) 203.0250. found 203.0252.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureunder refluxing for 2 hrs
  3. customthe reaction mixture was quenched with ice water
  4. extractionfollowed by extraction with AcOEt
  5. washThe organic layer was washed with brine
  6. dry with materialdried over NaSO4
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-a7b6ed51648248adb4d93116a83bd1b4
Quelldatensatz
uspto-grants-2007_12
Patentnummer
US07304074B2

Notizen zur Reaktion

Wird geladen…