Nitric Acid → Nimodipine Metabolite 3

HRID 247049Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 247049
[CH3:1][C:2]1[NH:3][C:4]([CH3:29])=[C:5]([C:23]([O:25][CH:26]([CH3:28])[CH3:27])=[O:24])[CH:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:7]=1[C:8]([O:10][CH2:11][CH2:12][OH:13])=[O:9].[N+]([O-])(O)=O.[OH-].[Na+]>O>[CH3:1][C:2]1[C:7]([C:8]([O:10][CH2:11][CH2:12][OH:13])=[O:9])=[C:6]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:5]([C:23]([O:25][CH:26]([CH3:27])[CH3:28])=[O:24])=[C:4]([CH3:29])[N:3]=1

Komponenten

5

Edukt 3

HCID 944Nitric AcidHCID 14798Sodium HydroxideHCID 104538601,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylic acid 3-isopropyl 5-(2-hydroxyethyl) ester

Produkt 1

HCID 10431202Nimodipine Metabolite 3

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

20 g (49.5 mmol) of 2-hydroxyethyl isopropyl 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate were introduced into a mixture of 83 ml of 96% strength nitric acid in 660 ml of water and heated to boiling for 1 hour. The mixture was then cooled down to 5° to 10° C. and made weakly alkaline with dilute sodium hydroxide solution. The oil which had separated out was extracted with methylene chloride, the extracts were dried over sodium sulphate and evaporated in vacuo. The oily residue was induced to crystallize by trituration with ether/petroleum ether, filtered off with suction and recrystallized from methanol.

Aufarbeitung

  1. temperatureheated
  2. temperatureThe mixture was then cooled down to 5° to 10° C.
  3. customThe oil which had separated out
  4. extractionwas extracted with methylene chloride
  5. dry with materialthe extracts were dried over sodium sulphate
  6. customevaporated in vacuo
  7. customto crystallize by trituration with ether/petroleum ether
  8. filtrationfiltered off with suction
  9. customrecrystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-007092b5341c459183e2d66331e5ea72
Quelldatensatz
uspto-grants-1987_11
Patentnummer
US04705794

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