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2-Butenoic acid, 3-amino-, 1-methylethyl ester → 4-(2-Cyanophenyl)-5-methoxycarbonyl-6-dimethoxymethyl-2-methyl-1,4-dihydropyridine-3-carboxylic acid

HRID 894724
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 894724
[C:1]([C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH:5]=[C:6]([C:11]([CH:13]([O:16][CH3:17])[O:14][CH3:15])=O)[C:7]([O:9][CH3:10])=[O:8])#[N:2].[NH2:22]/[C:23](/[CH3:31])=[CH:24]\[C:25]([O:27]C(C)C)=[O:26]>C(OCC)(=O)C>[C:1]([C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[CH:5]1[C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:11]([CH:13]([O:16][CH3:17])[O:14][CH3:15])[NH:22][C:23]([CH3:31])=[C:24]1[C:25]([OH:27])=[O:26])#[N:2]
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Komponenten

4

Edukt 2

HCID 111372742-Butenoic acid, 3-amino-, 1-methylethyl esterHCID 53675930Methyl 2-(2-cyanobenzylidene)-4,4-dimethoxyacetoacetate

Produkt 1

HCID 202772614-(2-Cyanophenyl)-5-methoxycarbonyl-6-dimethoxymethyl-2-methyl-1,4-dihydropyridine-3-carboxylic acidAusbeute 68,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of methyl 2-(2-cyanobenzylidene)-4,4-dimethoxyacetoacetate (10.1 g) and isopropyl 3-aminocrotonate (5.51 g) was heated for 40 minutes at 78° C. for 5.5 hours at 120° C. with stirring, followed by heating for an hour at 125° C. without the stirring. After the reaction mixture was allowed to stand overnight, it was dissolved in ethyl acetate. This solution was washed twice with water, dried and then evaporated to dryness under reduced pressure to give a residue, which was crystallized from ethyl ether. The crystals were collected by filtration and washed with a small amount of ethyl ether to give crude powder of isopropyl ester of 4-(2-cyanophenyl)-5-methoxycarbonyl-6-dimethoxymethyl-2-methyl-1,4-dihydropyridine-3-carboxylic acid (8.96 g.). Further, the crude product (0.77 g) was recovered from the filtrate. 0.5 g of this crude product was recrystallized from isopropyl ether to give purified white powder of the same product (0.37 g), mp 171°-172.5° C.

Aufarbeitung

  1. temperatureby heating for an hour at 125° C. without the stirring
  2. washThis solution was washed twice with water
  3. customdried
  4. customevaporated to dryness under reduced pressure
  5. customto give a residue, which
  6. customwas crystallized from ethyl ether
  7. filtrationThe crystals were collected by filtration
  8. washwashed with a small amount of ethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-0af290375be04491a51692eb52411128
Quelldatensatz
uspto-grants-1981_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04284634

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