5-Fluoro-1-indanone → HCID 86762368, Verbindung

HRID 2369234Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369234
[CH3:1][C:2]1[CH:3]=[C:4]([NH:9]N)[CH:5]=[C:6]([CH3:8])[CH:7]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17](=O)[CH2:16][CH2:15]2>C(O)C.C(O)(=O)C>[F:11][C:12]1[CH:13]=[C:14]2[C:18]([CH2:17][C:16]3[C:3]4[C:2]([CH3:1])=[CH:7][C:6]([CH3:8])=[CH:5][C:4]=4[NH:9][C:15]=32)=[CH:19][CH:20]=1

Komponenten

5

Edukt 2

HCID 1365375-Fluoro-1-indanoneHCID 1810602(3,5-dimethylphenyl)hydrazine

Produkt 1

HCID 86762368HCID 86762368, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 3,5-dimethylphenylhydrazine (2.54 g, 14.7 mmol) and 5-fluoro-1-indanone (2.21 g, 14.7 mmol) in ethanol (24 mL) was added glacial acetic acid (3 drops). The solution was stirred at reflux (85° C.) for 15 minutes and cooled to room temperature. Ethanol was removed in vacuo and the resulting orange solid was dissolved in isopropanol (24 mL). Sulfuric acid (36N, 1.65 mL) was added via syringe and the mixture was stirred at reflux (90° C.) for 17 hours and subsequently cooled to room temperature. The solution was basified to pH 10 via addition of aqueous sodium hydroxide (2% by mass) resulting in the formation of a precipitate. The solid was collected by vacuum filtration to yield 47b in 76% crude yield (2.80 g, 11.2 mmol). Crude product was brought on to the next step without further purification. 1H NMR (400 MHz, CDCl3): δ 8.12 (s, 1H), 7.32-7.35 (dd, 1H, J=8.2, 5.2 Hz), 0.24-7.26 (m, 1H), 7.01-7.05 (m, 2H), 6.79 (s, 1H), 3.83 (s, 2H), 2.60 (s, 3H), 2.44 (s, 3H); 13C NMR (150 MHz, CDCl3): δ 160.7 (d, J=361.5), 150.0 (d, J=12.0 Hz), 140.9, 140.6, 131.8, 131.2, 128.9, 122.6, 122.3, 121.6 (d, J=4.5 Hz), 117.2 (d, J=13.5 Hz), 113.4 (d, J=25.5 Hz), 113.1 (d, J=25.5 Hz), 109.6, 31.7 (d, J=3.0 Hz), 21.8, 19.3; 19F NMR (CD3CD, 376 MHz): δ −117.9 (m).

Aufarbeitung

  1. temperaturecooled to room temperature
  2. customEthanol was removed in vacuo
  3. dissolutionthe resulting orange solid was dissolved in isopropanol (24 mL)
  4. additionSulfuric acid (36N, 1.65 mL) was added via syringe
  5. stirringthe mixture was stirred
  6. temperatureat reflux (90° C.) for 17 hours
  7. temperaturesubsequently cooled to room temperature
  8. additionThe solution was basified to pH 10 via addition of aqueous sodium hydroxide (2% by mass)
  9. customresulting in the formation of a precipitate
  10. filtrationThe solid was collected by vacuum filtration

Quellen und Nachweise

ORD-Eintrag
ord-827dbd6524704bf1b3c6ceef37cc3b13
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08703936B2

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