4-Amino-1,2-dihydropyridin-2-one → 3-Acetyl-2-methyl-4-[4-nitro-2-(trifluoromethyl)phenyl]-4,6-dihydro-1,6-naphthyridin-5(1H)-one

HRID 1951388

Reaktionsgleichung

Reaktionsgleichung von HRID 1951388
[N+:1]([C:4]1[CH:17]=[CH:16][C:7]([CH:8]=[C:9]([C:13](=[O:15])[CH3:14])[C:10](=O)[CH3:11])=[C:6]([C:18]([F:21])([F:20])[F:19])[CH:5]=1)([O-:3])=[O:2].[NH2:22][C:23]1[CH:28]=[CH:27][NH:26][C:25](=[O:29])[CH:24]=1>C(O)(C)C>[C:13]([C:9]1[CH:8]([C:7]2[CH:16]=[CH:17][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=2[C:18]([F:19])([F:20])[F:21])[C:24]2[C:25](=[O:29])[NH:26][CH:27]=[CH:28][C:23]=2[NH:22][C:10]=1[CH3:11])(=[O:15])[CH3:14]

Komponenten

4

Edukt 2

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 596030233-[4-Nitro-2-(trifluoromethyl)benzylidene]pentane-2,4-dione

Produkt 1

HCID 596030333-Acetyl-2-methyl-4-[4-nitro-2-(trifluoromethyl)phenyl]-4,6-dihydro-1,6-naphthyridin-5(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

1.28 g (4.24 mmol) of 3-[4-nitro-2-(trifluoromethyl)benzylidene]pentane-2,4-dione and 484 mg (4.24 mmol) of 4-aminopyridin-2(1H)-one [Searls, T., McLaughlin, L. W., Tetrahedron 55, 11985-11996 (1999)] are dissolved in 25 ml of isopropanol and heated under reflux under argon for 12 h. Cooling is followed by filtration, and the remaining solid is washed with diethyl ether (40 ml). 990 mg (58% of theory) of the title compound are obtained as a white solid.

Aufarbeitung

  1. temperatureheated
  2. temperatureunder reflux under argon for 12 h
  3. temperatureCooling
  4. filtrationis followed by filtration
  5. washthe remaining solid is washed with diethyl ether (40 ml)

Quellen und Nachweise

ORD-Eintrag
ord-7f9f1533215c4828930e23cbdfe42c8d
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404709B2

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