Methylhydrazine → 1-Methyl-3-Pyridin-2-Yl-1H-Pyrazol-5-Amine

HRID 1748794Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1748794
O=[C:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=1)[CH2:3][C:4]#[N:5].[CH3:12][NH:13][NH2:14]>C(O)C>[CH3:12][N:13]1[C:4]([NH2:5])=[CH:3][C:2]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][N:7]=2)=[N:14]1

Komponenten

4

Edukt 2

HCID 6061MethylhydrazineHCID 115718233-Oxo-3-(pyridin-2-yl)propanenitrile

Produkt 1

HCID 133248371-Methyl-3-Pyridin-2-Yl-1H-Pyrazol-5-AmineAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of crude 3-oxo-3-(2-pyridyl)propanenitrile (48.6 g, 331 mmol) in ethanol (500 mL) was added methyl hydrazine (25 g, 543 mmol). The resulting mixture was stirred for about 30 min at rt and then heated at about 75° C. for about 18 h. After cooling to rt the reaction mixture was concentrated in vacuo. The residue was treated with toluene (300 mL). The formed solid was collected by filtration and washed with toluene (150 mL). The solid was dried under vacuum to give 1-methyl-3-(2-pyridyl)pyrazol-5-amine (36.2 g, 208 mmol, 63%). 1H-NMR (CDCl3, Bruker 400 MHz) δ 3.62 (3H, s); 5.34 (2H, br s); 5.90 (1H, s); 7.21 (1H, m); 7.73 (1H, dt, J=10 Hz, 2 Hz); 7.83 (1H, dt, J=10 Hz, 1 Hz); 8.51 (1H, dt, J=6 Hz, 2 Hz).

Aufarbeitung

  1. temperatureheated at about 75° C. for about 18 h
  2. temperatureAfter cooling to rt the reaction mixture
  3. concentrationwas concentrated in vacuo
  4. additionThe residue was treated with toluene (300 mL)
  5. filtrationThe formed solid was collected by filtration
  6. washwashed with toluene (150 mL)
  7. customThe solid was dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-3f82351a0a174617aff690a16ec2873f
Quelldatensatz
uspto-grants-2015_10
Patentnummer
US09150592B2

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