3-Aminopropionitrile → Ethyl 7-chloro-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

HRID 1696935Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1696935
Cl[C:2]1[C:7]([C:8](/[C:10](=[CH:16]/[N:17]([CH3:19])C)/[C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])=[CH:6][CH:5]=[C:4]([Cl:20])[N:3]=1.[NH2:21][CH2:22][CH2:23]C#N>C(O)C.C(OCC)C>[Cl:20][C:4]1[N:3]=[C:2]2[C:7]([C:8](=[O:9])[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:16][N:17]2[CH2:19][CH2:23][C:22]#[N:21])=[CH:6][CH:5]=1

Komponenten

4

Edukt 2

HCID 16473-AminopropionitrileHCID 15675736Ethyl (2Z)-2-((2,6-dichloropyridin-3-yl)carbonyl)-3-(dimethylamino)prop-2-enoate

Produkt 1

HCID 87333475Ethyl 7-chloro-1-(2-cyanoethyl)-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21585056Diethyl ether ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

A solution of EXAMPLE 81A (20 g) and 3-aminopropionitrile (4.9 mL) in 1:1 ethanol/diethyl ether (400 mL) was stirred for 15 minutes, diluted with hexanes (1 L), and filtered. The filtrant was dissolved in acetonitrile (400 mL), and the resulting solution was treated with potassium carbonate (17.4 g), heated at 75° C. for 18 hours then cooled, diluted with water (1.5 L), stirred for 1 hour, and filtered.

Aufarbeitung

  1. filtrationfiltered
  2. dissolutionThe filtrant was dissolved in acetonitrile (400 mL)
  3. additionthe resulting solution was treated with potassium carbonate (17.4 g)
  4. temperaturethen cooled
  5. additiondiluted with water (1.5 L)
  6. filtrationfiltered

Quellen und Nachweise

ORD-Eintrag
ord-2d11fef41e544d75b34d55a10652b3f1
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163769B2

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