3-Nitrobenzaldehyde → Diethyl 1,2,3,4-tetrahydro-2-hydroxy-6-methyl-4-(3-nitrophenyl)-2-(trifluoromethyl)-3,5-pyridine-dicarboxylate

HRID 364953

Reaktionsgleichung

Reaktionsgleichung von HRID 364953
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[NH2:12][C:13]([CH3:20])=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[F:21][C:22]([F:32])([F:31])[C:23](=[O:30])[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>C(O)C>[OH:30][C:23]1([C:22]([F:31])([F:32])[F:21])[CH:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[NH:12]1

Komponenten

5

Edukt 3

HCID 74493-NitrobenzaldehydeHCID 67793Ethyl 4,4,4-trifluoroacetoacetateHCID 953082-Butenoic acid, 3-amino-, ethyl ester

Produkt 1

HCID 20189336Diethyl 1,2,3,4-tetrahydro-2-hydroxy-6-methyl-4-(3-nitrophenyl)-2-(trifluoromethyl)-3,5-pyridine-dicarboxylateAusbeute 21,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

3-Nitrobenzaldehyde (3.0 g, 20 mmoles), ethyl 3-amino-2-butenoate (2.6 g, 20 mmoles) and ethyl 4,4,4-trifluoro-3-oxobutanoate (2.92 ml, 20 mmoles) were heated at reflux in ethanol (25 ml) for 6 hours. The solvent was removed in vacuo and the residue crystallised by the addition of ether/petroleum ether (60°-80°). The resulting solid was recrystallised from ether/petroleum ether (60°-80°) to give the title compound as colourless crystals (1.9 g) mp 120°-1°.

Aufarbeitung

  1. customThe solvent was removed in vacuo
  2. customthe residue crystallised by the addition of ether/petroleum ether (60°-80°)
  3. customThe resulting solid was recrystallised from ether/petroleum ether (60°-80°)

Quellen und Nachweise

ORD-Eintrag
ord-06f20a5dd9a44b7abc75750ac250ae5c
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04607041

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