Ammonia → 3-cyclopropylmethyl 5-[2-[N-(4-methoxybenzyl)-N-methylamino]ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate

HRID 621540Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 621540
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)[CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:21]([C:24]1[CH:25]=[C:26]([CH:39]=[CH:40][CH:41]=1)[CH:27]=[C:28]([C:36]([CH3:38])=O)[C:29]([O:31][CH2:32][CH:33]1[CH2:35][CH2:34]1)=[O:30])([O-:23])=[O:22].[NH3:42]>C(O)C>[CH3:38][C:36]1[NH:42][C:3]([CH3:5])=[C:2]([C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH3:11])=[O:6])[CH:27]([C:26]2[CH:39]=[CH:40][CH:41]=[C:24]([N+:21]([O-:23])=[O:22])[CH:25]=2)[C:28]=1[C:29]([O:31][CH2:32][CH:33]1[CH2:35][CH2:34]1)=[O:30]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 99937542-[N-(4-methoxybenzyl)-N-methylamino]-ethyl acetoacetateHCID 53956239Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate

Produkt 1

HCID 141000943-cyclopropylmethyl 5-[2-[N-(4-methoxybenzyl)-N-methylamino]ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateAusbeute 46,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 8.8 g (30 mmol) of 2-[N-(4-methoxybenzyl)-N-methylamino]-ethyl acetoacetate, 8.5 g (30 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate, 2.5 ml of 28% aqueous ammonia and 50 ml of ethanol was stirred at the reflux temperature for 7 hours, and then the solvent was removed under reduced pressure. The residue was chromatographed on silica gel column to afford 3-cyclopropylmethyl 5-[2-[N-(4-methoxybenzyl)-N-methylamino]ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (7.8 g, 46.7%) as yellow oil. Treatment of this oil with 1 equivalent of fumaric acid in ethanol gave the corresponding fumarate.

Aufarbeitung

  1. customthe solvent was removed under reduced pressure
  2. customThe residue was chromatographed on silica gel column

Quellen und Nachweise

ORD-Eintrag
ord-421a5e6b1cbb46c884b4372d8c7a8390
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824855

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