Hydrazine hydrate (1:1) → Diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

HRID 4661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 4661
[CH2:1]([C:3]1[NH:4][C:5]([CH3:44])=[C:6]([C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH:7]([C:14]2[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[CH:17]=[CH:16][C:15]=2[O:23][CH2:24][CH2:25][CH2:26][CH2:27][N:28]2C(=O)C3=CC=CC=C3C2=O)[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].O.NN>C(O)C>[NH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O:23][C:15]1[CH:16]=[CH:17][C:18]([N+:20]([O-:22])=[O:21])=[CH:19][C:14]=1[CH:7]1[C:6]([C:39]([O:41][CH2:42][CH3:43])=[O:40])=[C:5]([CH3:44])[NH:4][C:3]([CH2:1][CH3:2])=[C:8]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Komponenten

4

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 20151538Diethyl 2-ethyl-4-[2-(4-phthalimidobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Produkt 1

HCID 14050495Diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylateAusbeute 65,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 12.4 g of diethyl 2-ethyl-4-[2-(4-phthalimidobutoxy)-5-nitrophenyl]-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate and 10.4 g of hydrazine monohydrate in 270 ml of 95% ethanol (water: 5%) was refluxed under heating for 10 hours. After cooling the reaction solution, the solution was concentrated under reduced pressure, and the residue was extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. Crude crystals thus obtained were recrystallized from chloroform-ether to give 6.4 g of diethyl 4-[2-(4-aminobutoxy)-5-nitrophenyl]-2-ethyl-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate.

Aufarbeitung

  1. temperatureunder heating for 10 hours
  2. temperatureAfter cooling the reaction solution
  3. concentrationthe solution was concentrated under reduced pressure
  4. extractionthe residue was extracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customCrude crystals thus obtained
  9. customwere recrystallized from chloroform-ether

Quellen und Nachweise

ORD-Eintrag
ord-ae47bef14953469995ecbc681d8031ce
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04727082

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