Sodium Hydroxide → (R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

HRID 47266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 47266
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C@H:13]([CH3:19])[CH2:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1.O.O.[Sn](Cl)Cl.[OH-].[Na+]>O.Cl>[NH:5]([C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C@H:13]([CH3:19])[CH2:14][C:15](=[O:18])[NH:16][N:17]=2)=[CH:8][CH:7]=1)[NH2:1]

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 10465484(R)-6-(4-Aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)-oneHCID 23668193Sodium Nitrite

Produkt 1

HCID 69529174(R)-6-(4-hydrazino-phenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 313Hydrochloric AcidLösungsmittel2×HCID 962WaterLösungsmittel

Versuchsvorschrift

A slight modification on the procedure described in J.Med.Chem. (1990), 33(10), 2870-2875 was used as follows. A solution of sodium nitrite (1.7 g) in water (12.5 ml) was added slowly at 0-5° C. to a solution of (R)-6-(4-aminophenyl)-5-methyl-4,5-dihydro-2H-pyridazin-3-one (5 g) in 1 M hydrochloric acid (75 ml). The resulting solution was stirred on ice bath for five minutes and then added slowly to a solution of tin(II)chloride dihydrate (17 g) in 1 M hydrochloric acid (150 ml) keeping the reaction temperature below 5° C. This solution was stirred on ice for forty minutes and then a solution of 50% NaOH (75 ml) was quickly added. The resulting mixture was stirred on ice bath until the temperature reached zero degrees Celsius. The crystals were filtered and washed with dilute ammonia. Yield: 5.0 g, 93%.

Aufarbeitung

  1. customthe reaction temperature below 5° C
  2. stirringThis solution was stirred on ice for forty minutes
  3. stirringThe resulting mixture was stirred on ice bath until the temperature
  4. customreached zero degrees Celsius
  5. filtrationThe crystals were filtered
  6. washwashed with dilute ammonia

Quellen und Nachweise

ORD-Eintrag
ord-036ea9b989af47d9945eeb715a41bb5a
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699868B2

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