Reaktion #565925

ord-a2d9039d07cf4aabad7c6fecc8cadb52

Reaktionsgleichung

O=Cc1cccnc1Nc1cccc([N+](=O)[O-])c1
2-(3-nitrophenylamino)nicotinaldehyde
COC(=O)CCCc1ccncc1
methyl 4-(pyridin-4-yl)butanoate
CC(C)[N-]C(C)C.[Li+]
LDA
→
O=c1c(CCc2ccncc2)cc2cccnc2n1-c1cccc([N+](=O)[O-])c1
1-(3-nitrophenyl)-3-[2-(pyridin-4-yl)ethyl]-1,8-naphthyridin-2(1H)-one

Edukte

O=Cc1cccnc1Nc1cccc([N+](=O)[O-])c1
2-(3-nitrophenylamino)nicotinaldehyde
COC(=O)CCCc1ccncc1
methyl 4-(pyridin-4-yl)butanoate
CC(C)[N-]C(C)C.[Li+]
LDA

Reagenzien

Keine

Lösungsmittel

CCO.CN(C)C=O
DMF EtOH

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

The procedure of Example 1 was repeated using 2-(3-nitrophenylamino)nicotinaldehyde (1.0 eq.), methyl 4-(pyridin-4-yl)butanoate (1.1 eq., prepared in Synthetic Example 8) and LDA (1.5 eq.) to obtain 1-(3-nitrophenyl)-3-[2-(pyridin-4-yl)ethyl]-1,8-naphthyridin-2(1H)-one, mp 213 to 214° C./DMF-EtOH.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06642250B2uspto-grants-2003_11