Hydrochloric Acid → 1-(2,3-Dihydroxypropyl)-7-(methyloxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-one

HRID 1943136Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1943136
CC(C)(C)C([N:5]([CH2:23][CH:24]1[CH2:28][O:27]C(=O)[O:25]1)[C:6]1[C:11]([CH2:12][CH2:13][C:14](OCCCC)=[O:15])=[CH:10][CH:9]=[C:8]([O:21][CH3:22])[N:7]=1)=O.Cl>CO>[OH:25][CH:24]([CH2:28][OH:27])[CH2:23][N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[C:8]([O:21][CH3:22])[N:7]=2)[CH2:12][CH2:13][C:14]1=[O:15]

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 68596362Butyl 3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]propanoate

Produkt 1

HCID 685974381-(2,3-Dihydroxypropyl)-7-(methyloxy)-3,4-dihydro-1,8-naphthyridin-2(1H)-oneAusbeute 66,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of butyl 3-[2-{(2,2-dimethylpropanoyl)[(2-oxo-1,3-dioxolan-4-yl)methyl]amino}-6-(methyloxy)-3-pyridinyl]propanoate (6.065 g, 13.911 mmol) in methanol (100 ml) was treated with concentrated aqueous HCl (12M, 50 ml) and then heated at reflux for 48 h. The reaction mixture was then concentrated to approximately 50 ml, neutralised with potassium carbonate and extracted with 20% methanol/DCM (3×100 ml). The organic extracts were dried (MgSO4), and evaporated to give the crude product as a yellow oil (2.325 g, 66%).

Aufarbeitung

  1. temperatureheated
  2. temperatureat reflux for 48 h
  3. concentrationThe reaction mixture was then concentrated to approximately 50 ml
  4. extractionextracted with 20% methanol/DCM (3×100 ml)
  5. dry with materialThe organic extracts were dried (MgSO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-2c9c46ade3e14c6a8bd0df1028ab551a
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08389524B2

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