Formic Acid → 1-(5-Chloro-2-methoxyphenyl)ethanamine

HRID 2425994Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2425994
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([C:8](=O)[CH3:9])[CH:7]=1.C(O)=O.C([NH2:18])=O>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:8]([NH2:18])[CH3:9])[CH:7]=1

Komponenten

5

Edukt 3

HCID 284Formic AcidHCID 713FormamideHCID 2404341-(5-Chloro-2-methoxyphenyl)ethanone

Produkt 1

HCID 45381491-(5-Chloro-2-methoxyphenyl)ethanamine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1-(5-Chloro-2-methoxyphenyl)ethanone (6.7 g, 36.3 mmol) and formic acid (1.74 g, 27.7 mmol) were heated in formamide (10 mL) at 170° C. for 20 h. The mixture was cooled to room temperature, diluted with water and extracted with benzene. After removal of benzene by rotary evaporation the crude mixture was heated under reflux conditions in 3M HCl for 30 h. After cooling, the reaction was added to ether and extracted. The aqueous layer was basified with NaOH to pH 9 and extracted with dichloromethane. The dichloromethane was evaporated to collect the title compound (2.7 g, 40%). 1H NMR (400 MHz, CDCl3): δ 7.39 (d, 1H), 7.26 (q, 1H), 6.81 (d, 1H), 4.62 (m, 1H), 3.84 (s, 3H), 1.69 (d, 3H).

Aufarbeitung

  1. extractionextracted with benzene
  2. customAfter removal of benzene
  3. customby rotary evaporation the crude mixture
  4. temperaturewas heated under reflux conditions in 3M HCl for 30 h
  5. temperatureAfter cooling
  6. additionthe reaction was added to ether
  7. extractionextracted
  8. extractionextracted with dichloromethane
  9. customThe dichloromethane was evaporated
  10. customto collect the title compound (2.7 g, 40%)

Quellen und Nachweise

ORD-Eintrag
ord-a596026274b34fc0bac63fee60a6b467
Quelldatensatz
uspto-grants-2011_06
Patentnummer
US07968538B2

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