Ammonia → 3-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2-methyl-6-phenyl-3,5-pyridinedicarboxylate

HRID 364959

Reaktionsgleichung

Reaktionsgleichung von HRID 364959
N.[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:10]=[C:11]([C:16](=O)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:12]([O:14][CH3:15])=[O:13].[NH2:24][C:25]([CH3:32])=[CH:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>C(O)(C)(C)C>[Cl:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[CH:10]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:16]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[NH:24][C:25]([CH3:32])=[C:26]1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 953082-Butenoic acid, 3-amino-, ethyl esterHCID 54098640Methyl alpha-(2,3-dichlorophenylmethylene)-beta-oxobenzenepropanoate

Produkt 1

HCID 867409623-Ethyl 5-methyl 4-(2,3-dichlorophenyl)-1,4-dihydro-2-methyl-6-phenyl-3,5-pyridinedicarboxylateAusbeute 9,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Ammonia (0.5 ml, d=0.88) was added to a solution of methyl alpha-(2,3-dichlorophenylmethylene)-beta-oxobenzenepropanoate (2 g, 7.3 mmoles) and ethyl 3-amino-2-butenoate (0.77 g, 6.0 mmoles) in tert. butanol (8 ml) at 60°. The reaction was maintained at this temperature for 16 hours. The solvent was removed in vacuo and the residue was chromatographed on silica eluting with ethyl acetate/petroleum ether (60°-80°) mixtures. The title compound (0.25 g) was obtained after crystallisation from 2-propanol mp 185°-6°.

Aufarbeitung

  1. temperatureThe reaction was maintained at this temperature for 16 hours
  2. customThe solvent was removed in vacuo
  3. customthe residue was chromatographed on silica eluting with ethyl acetate/petroleum ether (60°-80°)

Quellen und Nachweise

ORD-Eintrag
ord-ca6b758a41b1446a97835c9225682751
Quelldatensatz
uspto-grants-1986_08
Patentnummer
US04607041

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