Ethanol → 1,4,5,6,7,8-Hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester

HRID 2059087Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2059087
[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].[C:24]1([CH3:32])[C:25]([CH:30]=O)=[CH:26][CH:27]=[CH:28][CH:29]=1.C(O)C>C(O)(=O)C>[CH3:16][O:17][C:18]([C:19]1[CH:32]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[CH3:30])[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

6

Edukt 4

HCID 702EthanolHCID 107222-MethylbenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 129006921-Benzyl-5-hydroxy-1,6-dihydropyridin-3(2H)-one

Produkt 1

HCID 128184551,4,5,6,7,8-Hexahydro-2-methyl-4-(2-methylphenyl)-5-oxo-7-(phenylmethyl)-1,7-naphthyridine-3-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of 6.1 g. of 1-benzyl-3-oxo-5-hydroxy-1,2,3,6-tetrahydropyridine, 3.6 g. of methyl-3-aminocrotonate (97%), 3.6 g. of o-tolualdehyde, 55 ml. of ethanol and 18 ml. of acetic acid was refluxed for 7 hours. The solution was evaporated to dryness in vacuo. The residue was triturated with diethyl ether and the solid was separated by filtration. Recrystallization from ethanol afforded the title compound, m.p. 201°-204° C.

Aufarbeitung

  1. additionA mixture of 6.1 g
  2. customThe solution was evaporated to dryness in vacuo
  3. customThe residue was triturated with diethyl ether
  4. customthe solid was separated by filtration
  5. customRecrystallization from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-54200fc560884c8bb698f0b19a1e03a8
Quelldatensatz
uspto-grants-1982_03
Patentnummer
US04321384

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