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2-Methoxyethyl acetoacetate → Isopropyl 2-methoxyethyl 4-(3-amino-2-chloro-phenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate

HRID 1653682
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1653682
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[CH:6][CH:5]=[CH:4][C:3]=1[CH:11]1[C:16]([C:17]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[O:18])=[C:15]([CH3:24])[NH:14][C:13]([CH3:25])=[C:12]1[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27].ClC1C([N+]([O-])=O)=CC=CC=1C=O.N/C(/C)=C\C(OC(C)C)=O.C(OCCOC)(=O)CC(C)=O>CC(O)C>[NH2:8][C:7]1[C:2]([Cl:1])=[C:3]([CH:11]2[C:16]([C:17]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[O:18])=[C:15]([CH3:24])[NH:14][C:13]([CH3:25])=[C:12]2[C:26]([O:28][CH:29]([CH3:30])[CH3:31])=[O:27])[CH:4]=[CH:5][CH:6]=1
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Komponenten

6

Edukt 4

HCID 897342-Methoxyethyl acetoacetateHCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl esterHCID 126677132-Chloro-3-nitrobenzaldehydeHCID 67785793Isopropyl 2-methoxy-ethyl 4-(2-chloro-3-nitrophenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate

Produkt 1

HCID 20080473
Isopropyl 2-methoxyethyl 4-(3-amino-2-chloro-phenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

Isopropyl 2-methoxyethyl 4-(3-amino-2-chloro-phenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate ##STR31## 27.5 g (61 mmol, purity 96.5%) of isopropyl 2-methoxy-ethyl 4-(2-chloro-3-nitrophenyl)-1,4-dihydro-2,6-dimethyl-pyridine-3,5-dicarboxylate, obtained by reaction of equimolar amounts of 2-chloro-3-nitrobenzaldehyde, isopropyl β-aminocrotonate and methoxyethyl acetoacetate in 2-propanol at the reflux temperature, are suspended in 500 ml of methanol and hydrogenated in the presence of Raney nickel (about 1.5 g, water-moist) under normal pressure and temperature until the end of the uptake of hydrogen (1 hour). The catalyst is filtered off and the residue obtained after concentration is purified by flash chromatography (toluene/ethyl acetate 1:0→5:1). Crystallization from toluene gives 24.0 g (93% of theory) of the title compound of melting point 118°-122° C.

Quellen und Nachweise

ORD-Eintrag
ord-ce86b4407eed4039b5931cbb7ea0cb37
Quelldatensatz
uspto-grants-1995_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05403849

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