Formic acid (ammonium salt) → 3-(7-Anilino-2-methyl-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridin-3-yl)propanoic acid

HRID 2183812

Reaktionsgleichung

Reaktionsgleichung von HRID 2183812
[NH:1]([C:8]1[N:9]([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:10]2[C:15]([C:16](=[O:18])[CH:17]=1)=[CH:14][C:13](/[CH:19]=[CH:20]/[C:21]([OH:23])=[O:22])=[C:12]([CH3:24])[N:11]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)=O.N>CO.[Pd]>[NH:1]([C:8]1[N:9]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:10]2[N:11]=[C:12]([CH3:24])[C:13]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])=[CH:14][C:15]=2[C:16](=[O:18])[CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 10904Formic acid (ammonium salt)HCID 21948149HCID 21948149, Verbindung

Produkt 1

HCID 222789453-(7-Anilino-2-methyl-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridin-3-yl)propanoic acidAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred suspension of 2-anilino-6-[(E)-3-hydroxy-3-oxo-1-propenyl]-7-methyl-1-phenyl-1,8-naphthyridin-4(1H)-one (40.0 mg, 0.100 mmol) in MeOH (2.0 mL), was added Pd/C (5.3 mg, 10% weight on carbon) under an argon atmosphere, followed by the addition of ammonia formate (19.0 mg, 0.30 mmol) in a single portion. The reaction mixture was heated at reflux for 2 h, cooled and filtered. The filtrate was diluted with water (10 mL) and extracted with EtOAc. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was washed with water and dried in vacuo to afford 3-(7-anilino-2-methyl-5-oxo-8-phenyl-5,8-dihydro-1,8-naphthyridin-3-yl)propanoicacid (34.5 mg, 86%): LCMS RT: 2.31 min, MH+: 400.4, Rf=0.61 (4:1 EtOAc:MeOH).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2 h
  3. temperaturecooled
  4. filtrationfiltered
  5. additionThe filtrate was diluted with water (10 mL)
  6. extractionextracted with EtOAc
  7. dry with materialThe organic layer was dried over MgSO4
  8. concentrationconcentrated in vacuo
  9. washThe residue was washed with water
  10. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bdb6f183837443a88af1b15b04344c9e
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900205B2

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