o-(Trifluoromethyl)benzaldehyde → 1,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester

HRID 2059088Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059088
[CH2:1]([N:8]1[CH2:13][C:12](O)=[CH:11][C:10](=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][O:17][C:18](=[O:23])/[CH:19]=[C:20](\[NH2:22])/[CH3:21].[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][CH:31]=[CH:30][C:27]=1[CH:28]=O>C(O)C>[CH3:16][O:17][C:18]([C:19]1[CH:28]([C:27]2[CH:30]=[CH:31][CH:32]=[CH:33][C:26]=2[C:25]([F:24])([F:34])[F:35])[C:11]2[C:10](=[O:15])[CH2:9][N:8]([CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH2:13][C:12]=2[NH:22][C:20]=1[CH3:21])=[O:23]

Komponenten

5

Edukt 3

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 129006921-Benzyl-5-hydroxy-1,6-dihydropyridin-3(2H)-one

Produkt 1

HCID 128184561,4,5,6,7,8-Hexahydro-2-methyl-5-oxo-7-(phenylmethyl)-4-[2-(trifluoromethyl)phenyl]-1,7-naphthyridine-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 8.5 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 4.75 g. of methyl-3-aminocrotonate (97%), 6.96 g. of o-trifluoromethylbenzaldehyde and 125 ml. of ethanol was refluxed for 2 hours. The mixture was filtered while hot and the filtrate was allowed to cool to room temperature. The solid was separated by filtration. Recrystallization from ethanol afforded the title compound, m.p. 225°-227° C.

Aufarbeitung

  1. additionA mixture of 8.5 g
  2. filtrationThe mixture was filtered while hot and the filtrate
  3. customThe solid was separated by filtration
  4. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-4215ce00b30f4b349d48016b7d4e008c
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04321384

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