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

HRID 621537Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 621537
[C:1]([O:7][CH2:8][CH2:9][N:10]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH3:11])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[N+:19]([C:22]1[CH:23]=[C:24]([CH:37]=[CH:38][CH:39]=1)[CH:25]=[C:26]([C:34]([CH3:36])=O)[C:27]([O:29][CH2:30][CH:31]1[CH2:33][CH2:32]1)=[O:28])([O-:21])=[O:20].[NH3:40]>C(O)C>[CH3:36][C:34]1[NH:40][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][CH:16]=[CH:15][CH:14]=2)[CH3:11])=[O:6])[CH:25]([C:24]2[CH:37]=[CH:38][CH:39]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:26]=1[C:27]([O:29][CH2:30][CH:31]1[CH2:33][CH2:32]1)=[O:28]

Komponenten

5

Edukt 3

HCID 222AmmoniaHCID 117768292-(Benzylmethylamino)ethyl acetoacetateHCID 53956239Cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate

Produkt 1

HCID 30659143-cyclopropylmethyl 5-[2-(N-benzyl-N-methylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylateAusbeute 42,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture of 4.0 g (16 mmol) of 2-(N-benzyl-N-methylamino)ethyl acetoacetate, 4.6 g (16 mmol) of cyclopropylmethyl 2-(3-nitrobenzylidene)acetoacetate, 1.12 ml of 28% aqueous ammonia and 40 ml of ethanol was stirred at the reflux temperature for 8 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-benzyl-N-methylamino)ethyl] 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate (3.5 g, 42.1%) as yellow oil. Treatment of this oil with hydrochloric acid gave the corresponding salt.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-54e3911edb1240338130292957529339
Quelldatensatz
uspto-grants-1989_04
Patentnummer
US04824855

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