Hydrochloric Acid → FR 7534

HRID 614608Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 614608
[CH3:1][C:2]1[NH:3][C:4]([CH:27]=[O:28])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[BH4-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[NH:3][C:4]([CH2:27][OH:28])=[C:5]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:6]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 13388353HCID 13388353, Verbindung

Produkt 1

HCID 173874FR 7534Ausbeute 64,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a suspended solution of diethyl 2-methyl-4-(3-nitrophenyl)-6-formyl-1,4-dihydropyridine-3,5-dicarboxylate (233 mg) in ethanol (10 ml) was added sodium borohydride (22.7 mg) at 0° to 5° C under stirring and this mixture was further stirred at about 5° C. for an hour and 10 minutes. After the reaction, the mixture was adjusted to pH 4 to 5 with 0.1N-hydrochloric acid, and then the solvent was removed under reduced pressure. The residue was extracted with ethyl acetate and the extract was washed with water and dried over magnesium sulfate. The extract was concentrated under reduced pressure and the residue was crystallized by treating with a mixture of diethyl ether and n-hexane. The precipitated crystals were collected by filtration, dried and recrystallized from a mixture of diethyl ether and n-hexane to give crystals of diethyl 2-methyl-4-(3-nitrophenyl)-6-hydroxymethyl-1,4-dihydropyridine-3,5-dicarboxylate (152 mg), m.p. 141° to 142.5° C.

Aufarbeitung

  1. stirringthis mixture was further stirred at about 5° C. for an hour and 10 minutes
  2. customAfter the reaction
  3. customthe solvent was removed under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate
  5. washthe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe extract was concentrated under reduced pressure
  8. customthe residue was crystallized
  9. additionby treating with a mixture of diethyl ether and n-hexane
  10. filtrationThe precipitated crystals were collected by filtration
  11. customdried
  12. customrecrystallized from a mixture of diethyl ether and n-hexane

Quellen und Nachweise

ORD-Eintrag
ord-66390f6e5e91467795c2d5464ddd5304
Quelldatensatz
uspto-grants-1979_03
Patentnummer
US04145432

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