Ethyl benzoylacetate → HCID 178469958, Verbindung

HRID 386648

Reaktionsgleichung

Reaktionsgleichung von HRID 386648
[NH2:1][C:2]1[NH:6][N:5]=[CH:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].O=[C:13]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:14][C:15](OCC)=[O:16]>C(O)(=O)C>[OH:16][C:15]1[N:6]2[N:5]=[CH:4][C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]2[N:1]=[C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:14]=1

Komponenten

4

Edukt 2

HCID 7170Ethyl benzoylacetateHCID 81472ethyl 3-amino-1H-pyrazole-4-carboxylate

Produkt 1

HCID 178469958HCID 178469958, VerbindungAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Commercially available ethyl 5-amino-1H-pyrazole-4-carboxylate (5.0 g, 32 mmol) was taken into glacial acetic acid (3.2 mL) followed by addition of ethyl 3-oxo-3-phenylpropanoate (6.1 mL, 35 mmol) and the mixture was refluxed for 12 h. The mixture was allowed to cool to room temperature and concentrated in vacuo. The crude solid was recrystallized (ethanol) and collected to yield 3.1 g (61%) of crystalline ethyl 7-hydroxy-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylate. 1H NMR (400 MHz, d6-DMSO): 11.75 (s, 1H), 8.28 (s, 1H), 7.80 (m, 2H), 7.61 (m, 3H), 6.28 (s, 1H), 4.31 (q, 2H), 1.34 (t, 3H).

Aufarbeitung

  1. temperaturethe mixture was refluxed for 12 h
  2. concentrationconcentrated in vacuo
  3. customThe crude solid was recrystallized (ethanol)
  4. customcollected

Quellen und Nachweise

ORD-Eintrag
ord-d0ac4a62de4d465aa9805715d06346f8
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372851B2

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