Sulfuric Acid → 5-Methyl-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxamide

HRID 462712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 462712
S(=O)(=O)(O)O.[CH3:6][C:7]1[N:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[C:10]([C:18]#[N:19])[C:11](=[O:17])[NH:12]2.[OH-:20].[NH4+]>C(O)(=O)C>[CH3:6][C:7]1[N:16]=[CH:15][CH:14]=[C:13]2[C:8]=1[CH:9]=[C:10]([C:18]([NH2:19])=[O:20])[C:11](=[O:17])[NH:12]2

Komponenten

5

Edukt 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 57130685-methyl-2-oxo-1H-1,6-naphthyridine-3-carbonitrile

Produkt 1

HCID 132320465-Methyl-2-oxo-1,2-dihydro-1,6-naphthyridine-3-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

E-2 1,2-Dihydro-5-methyl-2-oxo-1,6-naphthyridine-3carboxamide--To 200 ml of concentrated sulfuric acid chilled in an ice bath was added with stirring 37 g of 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile and the reaction mixture was allowed to stand at room temperature overnight. The reaction mixture was then poured on ice (1 liter beaker, half filled), the resulting mixture cooled in an ice bath and then neutralized by adding aqueous ammonium hydroxide, followed by addition of acetic acid to make the mixture slightly acidic. The separated solid was collected, washed with water, air-dried, then recrystallized from a large volume of dimethylformamide (1.2 1.) and dried at 95° C. to yield 8.4 g of 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carboxamide, m.p.>320° C.

Aufarbeitung

  1. additionwas added
  2. additionThe reaction mixture was then poured on ice (1 liter beaker, half filled)
  3. temperaturethe resulting mixture cooled in an ice bath
  4. customThe separated solid was collected
  5. washwashed with water
  6. customair-dried
  7. customrecrystallized from a large volume of dimethylformamide (1.2 1.)
  8. customdried at 95° C.

Quellen und Nachweise

ORD-Eintrag
ord-5154aa68466a41998defe16737984bca
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04517190

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