Isopropylamine → 1-Isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

HRID 527335Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 527335
CN([CH:4]=[C:5]1[C:10](=[O:11])[CH:9]=[C:8]([CH3:12])[O:7][C:6]1=[O:13])C.[CH:14]([NH2:17])([CH3:16])[CH3:15].CC(C)([O-])C.[Na+]>C(O)C>[CH:14]([N:17]1[C:8]([CH3:12])=[CH:9][C:10](=[O:11])[C:5]([C:6]([OH:13])=[O:7])=[CH:4]1)([CH3:16])[CH3:15]

Komponenten

5

Edukt 3

HCID 6363IsopropylamineHCID 14897943-(Dimethylaminomethylidene)-6-methylpyran-2,4-dioneHCID 23676156Sodium t-butoxide

Produkt 1

HCID 835312711-Isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 3-dimethylaminomethylene-6-methyl-pyran-2,4-dione (preparation 1a, 10.00 g, 38.6 mmol based on 70% purity), isopropylamine (5.00 mL, 58.4 mmol) and sodium tert-butoxide (5.50 g, 57.2 mmol) in ethanol (20 mL) is heated for 18 h at 90° C. The reaction mixture is evaporated under reduced pressure, treated with water and extracted with dichloromethane. The aqueous layer is acidified with 4 N aqueous HCl and extracted with dichloromethane. The combined organic layer is washed with water, dried over Na2SO4 and evaporated under reduced pressure. Yield: 7.16 g; ESI mass spectrum: [M+H]+=196; r.t. HPLC: 0.71 min (Z002_006).

Aufarbeitung

  1. customThe reaction mixture is evaporated under reduced pressure
  2. additiontreated with water
  3. extractionextracted with dichloromethane
  4. extractionextracted with dichloromethane
  5. washThe combined organic layer is washed with water
  6. dry with materialdried over Na2SO4
  7. customevaporated under reduced pressure
  8. customr.t
  9. custom0.71 min (Z002_006)

Quellen und Nachweise

ORD-Eintrag
ord-97be5c8e8e754af49018285346dddb4e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346794B1

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