Ethyl Acetoacetate → HCID 178429159, Verbindung

HRID 348007Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 348007
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]([NH2:13])[NH:11][N:12]=1.[C:14](OCC)(=[O:19])[CH2:15][C:16]([CH3:18])=O>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[C:10]2[N:13]=[C:16]([CH3:18])[CH:15]=[C:14]([OH:19])[N:11]2[N:12]=1

Komponenten

4

Edukt 2

HCID 8868Ethyl AcetoacetateHCID 178507276HCID 178507276, Verbindung

Produkt 1

HCID 178429159HCID 178429159, VerbindungAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 5-(2-chlorophenyl)-2H-pyrazol-3-ylamine (I-1A-1a; 1.51 g, 7.80 mmol) in acetic acid (10 ml) was added ethyl acetoacetate (1.1 ml, 8.6 mmol). The reaction was heated at reflux for 17 hours. Upon cooling to room temperature a solid precipitate formed which, after standing for 2 days, was isolated by vacuum filtration and washed with additional acetic acid. The solids were stirred in ether and then isolated by vacuum filtration to afford I-1A-3f as a colorless solid (1.52 g, 75%): +ESI MS (M+1) 260.2; 1H NMR (400 MHz, DMSO-d6) δ 12.18 (br s, 1H), 7.85–7.81 (m, 1H), 7.57–7.54 (m, 1H), 7.46–7.41 (m, 2H), 6.49 (s, 1H), 5.61 (s, 1H), 2.29 (s, 3H).

Aufarbeitung

  1. temperatureThe reaction was heated
  2. temperatureat reflux for 17 hours
  3. customformed which
  4. customwas isolated by vacuum filtration
  5. washwashed with additional acetic acid
  6. customisolated by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-dceba46009ba42dbaa8c5a22867da96c
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176210B2

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