1-(Ethylamino)propan-2-ol → 1-(Ethyl(6-hydrazinylidene-1,6-dihydropyridazin-3-yl)amino)propan-2-ol--hydrogen chloride (1/2)

HRID 1380389Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1380389
[Cl:1][C:2]1[CH:13]=[CH:12][C:5]2=[N:6][N:7]=C(C)C(=O)[N:4]2[N:3]=1.[CH2:14]([NH:16][CH2:17][CH:18]([OH:20])[CH3:19])[CH3:15]>C1(C)C=CC=CC=1>[ClH:1].[ClH:1].[CH2:14]([N:16]([CH2:17][CH:18]([OH:20])[CH3:19])[C:2]1[N:3]=[N:4][C:5]([NH:6][NH2:7])=[CH:12][CH:13]=1)[CH3:15]

Komponenten

4

Edukt 2

HCID 30161641-(Ethylamino)propan-2-olHCID 13615148HCID 13615148, Verbindung

Produkt 1

HCID 30439651-(Ethyl(6-hydrazinylidene-1,6-dihydropyridazin-3-yl)amino)propan-2-ol--hydrogen chloride (1/2)Ausbeute 288,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution comprising 480 mg 7-chloro-3-methyl-4-oxo-4H-pyridazino[6,1-c][1,2,4]triazine and 510 mg ethyl-(2-hydroxypropyl)amine in 10 ml toluene is heated to reflux for two hours, toluene is removed by evaporation, the remaining part if taken up with acetone, filtered, and the filtrate concentrated to a small volume. After cooling, 400 mg 7-[ethyl-(2-hydroxypropyl)amino]-3-methyl-4-oxo-4H-pyridazino[6,1-c][1, 2,4]triazine are collected under a vacuum, which melts at 140°-145° C. 1.3 grams 7-[ethyl-(2-hydroxypropyl)amino]-3-methyl-4-oxo-4H-pyridazino[6,1-c][1,2,4]triazine and 1 gram 2,4-dinitrophenylhydrazine are heated, while stirring, to 60° C. for three hours in 60 ml of 15% hydrochloric acid. These are cooled to 0° C. overnight, collected under a vacuum and washed with cold water. The mother liquors, after filtering, are evaporated to a dry condition, the residue being taken up twice with n.butylic alcohol and each time re-evaporated. A solid product is obtained which is triturated with 10 ml n.butylic alcohol, cooled, and collected under vacuum to yield 1 g of 3-[ethyl-(2-hydroxypropyl)amino]-6-hydrazinopyridazine dihydrochloride melting (with decomposition) at 212° C.

Aufarbeitung

  1. temperatureis heated
  2. temperatureto reflux for two hours
  3. customtoluene is removed by evaporation
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated to a small volume
  6. temperatureAfter cooling
  7. custom400 mg 7-[ethyl-(2-hydroxypropyl)amino]-3-methyl-4-oxo-4H-pyridazino[6,1-c][1, 2,4]triazine are collected under a vacuum, which melts at 140°-145° C
  8. temperature1.3 grams 7-[ethyl-(2-hydroxypropyl)amino]-3-methyl-4-oxo-4H-pyridazino[6,1-c][1,2,4]triazine and 1 gram 2,4-dinitrophenylhydrazine are heated
  9. temperatureThese are cooled to 0° C. overnight
  10. customcollected under a vacuum
  11. washwashed with cold water
  12. filtrationThe mother liquors, after filtering
  13. customare evaporated to a dry condition
  14. customeach time re-evaporated
  15. customA solid product is obtained which
  16. customis triturated with 10 ml n.butylic alcohol
  17. temperaturecooled
  18. customcollected under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-31cec43512d143d08a480d04429c7c14
Quelldatensatz
uspto-grants-1986_04
Patentnummer
US04581449

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