Diethyl Malonate → HCID 135957256, Verbindung

HRID 1263492

Reaktionsgleichung

Reaktionsgleichung von HRID 1263492
[Na].[O-]CC.[Na+].[C:6]([O:14]CC)(=O)[CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9].[NH2:17][C:18]1[N:22]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[N:21]=[CH:20][C:19]=1[C:29]#[N:30]>C(O)C>[CH2:11]([O:10][C:8]([C:7]1[C:6](=[O:14])[NH:17][C:18]2[N:22]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:21]=[CH:20][C:19]=2[C:29]=1[NH2:30])=[O:9])[CH3:12]

Komponenten

6

Edukt 4

HCID 7761Diethyl MalonateHCID 792565-Amino-1-phenyl-1H-pyrazole-4-carbonitrileHCID 2723922Sodium ethoxideHCID 5360545Sodium

Produkt 1

HCID 135957256HCID 135957256, VerbindungAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

Sodium pellets (0.86 g, 37.4 mmol) were added carefully to dry ethanol (40 ml) in a round-bottomed flask with a condenser in place and under nitrogen. The resulting solution of sodium ethoxide was allowed to cool to room temperature before addition of diethyl malonate (4.74 ml, 31.2 mmol). 5-Amino-1-phenylpyrazole-4-carbonitrile (2.30 g, 12.5 mmol) was added portionwise and the mixture heated at reflux for 4 h. The mixture was cooled and the ethanol removed in vacuo. Water (25 ml) was added to the residue and the solid was filtered off, washing with water. 4-Amino-6,7-dihydro-6-oxo-1-phenyl-1H-pyrazolo [3,4-b]pyridine-5-carboxylic acid ethyl ester (1.5 g, 40%) was obtained as a white solid. δH (400 MHz; DMSO) 1.35 (3H, t, J=7), 4.40 (2H, q, J=7), 7.30-7.34 (1H, m), 7.49-7.54 (2H, m), 8.04 (2H, br s), 8.09 (2H, br d, J=8), 8.44 (1H, s), 12.20 (1H, br s).

Aufarbeitung

  1. temperaturethe mixture heated
  2. temperatureat reflux for 4 h
  3. temperatureThe mixture was cooled
  4. customthe ethanol removed in vacuo
  5. additionWater (25 ml) was added to the residue
  6. filtrationthe solid was filtered off
  7. washwashing with water

Quellen und Nachweise

ORD-Eintrag
ord-b793f04500c2441489ae50045a711a6b
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541484B2

Verknüpfte Notizen

Wird geladen…