Acetic Acid → 4-(2,4,6-Trimethyl-phenyl)-2H-pyrazol-3-ylamine

HRID 2183545

Reaktionsgleichung

Reaktionsgleichung von HRID 2183545
O=[CH:2][CH:3]([C:6]1[C:11]([CH3:12])=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=1[CH3:14])[C:4]#[N:5].O.[NH2:16][NH2:17].C(O)(=O)C.Cl>C1C=CC=CC=1.O>[CH3:14][C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[C:11]([CH3:12])[C:6]=1[C:3]1[CH:2]=[N:17][NH:16][C:4]=1[NH2:5]

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 224743973-Oxo-2-(2,4,6-trimethyl-phenyl)-propionitrile

Produkt 1

HCID 224743864-(2,4,6-Trimethyl-phenyl)-2H-pyrazol-3-ylamineAusbeute 10,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 3-oxo-2-(2,4,6-trimethyl-phenyl)-propionitrile (2.300 g, 12.3 mmol), hydrazine hydrate (0.93 g) and glacial acetic acid (1.55 ml) in 20 ml benzene was heated at reflux for 4.5 hours. Reaction mixture was cooled to room temperature and 50 ml of 18.5% HCl in water was added. The benzene layer was separated and reextracted with 18.5% HCl. The aqueous layer were combined and neutralized with ammonium hydroxide and stirred at rt. overnight. Precipitate formed and was filtered to yield the title compound (0.256 g) as a yellow solid. The benzene layer was concentrated and purified through silica gel column using 5% methanol in chloroform as eluent to give an additional 1.450 g of the title compound; 1H NMR (CDCl3) ä 7.24(s, 1H), 6.95(s, 2H), 4.75(brs, 2H), 2.32(s, 3H), 2.13(s, 6H) ppm.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4.5 hours
  3. customReaction mixture
  4. customThe benzene layer was separated
  5. customovernight
  6. customPrecipitate formed
  7. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-9b402513c4384f52b727e614cf322e46
Quelldatensatz
uspto-grants-2005_05
Patentnummer
US06900217B2

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