2-Hydrazinopyridine → 5-methyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl ester

HRID 604300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 604300
[CH2:1]([O:3][C:4](=[O:13])[C:5](=[CH:9]N(C)C)[C:6](=O)[CH3:7])[CH3:2].[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH:20][NH2:21]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:9]=[N:21][N:20]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][N:14]=2)[C:6]=1[CH3:7])=[O:13])[CH3:2]

Komponenten

4

Edukt 2

HCID 786452-HydrazinopyridineHCID 3806790Ethyl 2-acetyl-3-(dimethylamino)acrylate

Produkt 1

HCID 222675745-methyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl esterAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Dissolve 2-dimethylaminomethylene-3-oxo-butyric acid ethyl ester (0.662 g, 3.57 mmol) and pyridin-2-yl-hydrazine (0.410 g, 3.75 mmol) in ethanol (15 mL) and reflux for 2 hr. Evaporate the mixture then dilute with saturated sodium bicarbonate and extract three times with ethyl acetate. Dry the solution (sodium sulfate), filter and concentrate. Purify using silica gel chromatography, eluting with 50:50 ethyl acetate:hexane to give 5-methyl-1-pyridin-2-yl-1H-pyrazole-4-carboxylic acid ethyl ester as a white solid (0.700 g, 85%). MS (m/z): 232 (M+1).

Aufarbeitung

  1. temperaturereflux for 2 hr
  2. customEvaporate the mixture
  3. additionthen dilute with saturated sodium bicarbonate
  4. extractionextract three times with ethyl acetate
  5. dry with materialDry the solution (sodium sulfate)
  6. filtrationfilter
  7. concentrationconcentrate
  8. customPurify
  9. washeluting with 50:50 ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-067388ba85e74be4a2c5537d044bad48
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07910588B2

Notizen zur Reaktion

Wird geladen…