4-Amino-1,2-dihydropyridin-2-one → 4-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-methylbenzonitrile

HRID 1951396

Reaktionsgleichung

Reaktionsgleichung von HRID 1951396
[C:1]([C:4]([C:15](=[O:17])[CH3:16])=[CH:5][C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[CH3:14])(=O)[CH3:2].[NH2:18][C:19]1[CH:24]=[CH:23][NH:22][C:21](=[O:25])[CH:20]=1>C(O)(C)C>[C:15]([C:4]1[CH:5]([C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=2[CH3:14])[C:20]2[C:21](=[O:25])[NH:22][CH:23]=[CH:24][C:19]=2[NH:18][C:1]=1[CH3:2])(=[O:17])[CH3:16]

Komponenten

4

Edukt 2

HCID 5735304-Amino-1,2-dihydropyridin-2-oneHCID 596030304-(2-Acetyl-3-oxobut-1-en-1-yl)-3-methylbenzonitrile

Produkt 1

HCID 596030344-(3-Acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-methylbenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

1.10 g (4.84 mmol) of 4-(2-acetyl-3-oxobut-1-en-1-yl)-3-methylbenzonitrile are taken up in 30 ml of isopropanol and, after addition of 592 mg (4.84 mmol) of 4-aminopyridin-2(1H)-one, heated at the reflux temperature for 72 h. The mixture is then concentrated, and the residue is again taken up in isopropanol and filtered through silica gel with isopropanol as eluent. The residue after concentration of the filtrate is mixed with a little methanol and crystallized. The precipitated product is filtered off, washed with diethyl ether and dried under high vacuum. 348 mg (22.5% of theory) of the title compound are obtained.

Aufarbeitung

  1. temperatureheated at the reflux temperature for 72 h
  2. concentrationThe mixture is then concentrated
  3. filtrationfiltered through silica gel with isopropanol as eluent
  4. additionThe residue after concentration of the filtrate is mixed with a little methanol
  5. customcrystallized
  6. filtrationThe precipitated product is filtered off
  7. washwashed with diethyl ether
  8. customdried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-85d22559bcc74a54a10dbf79fd9b6e5a
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08404709B2

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