Sodium Hydroxide → (2-Aminophenyl)(cyclopropyl)methanone

HRID 365970

Reaktionsgleichung

Reaktionsgleichung von HRID 365970
Cl.[NH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9](=[O:14])[CH2:10][CH2:11][CH2:12]Cl.[OH-].[Na+]>C(Cl)Cl.C(Cl)CCl.[Cl-].C[N+](CCCC)(CCCC)CCCC>[CH:10]1([C:9]([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[NH2:2])=[O:14])[CH2:12][CH2:11]1

Komponenten

6

Edukt 2

HCID 14798Sodium HydroxideHCID 232932461-(o-Aminophenyl)-4-chloro-1-butanone hydrochloride

Produkt 1

HCID 10931741(2-Aminophenyl)(cyclopropyl)methanoneAusbeute 70 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 91822Tributylmethylammonium chlorideKatalysatorHCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

A solution of 0.30 g (1.3 mmol) of 1-(o-aminophenyl)-4-chloro-1-butanone hydrochloride in 3 mL of methylene chloride and 3 mL of ethylene dichloride is treated with 1.2 g (3 mmol) of 10% sodium hydroxide solution and 0.05 g (0.2 mmol) of 75% aqueous methyl tributylammonium chloride and heated to 50° C. for about 5 hours. After cooling to room temperature, the phases are separated. The aqueous layer is extracted with methylene chloride. The combined organic extracts are washed with water and concentrated in vacuo to give 0.14 g (70% yield) of o-aminophenyl cyclopropyl ketone (mp 46-48° C.). The product is identified by NMR and MS analyses.

Aufarbeitung

  1. temperatureAfter cooling to room temperature
  2. customthe phases are separated
  3. extractionThe aqueous layer is extracted with methylene chloride
  4. washThe combined organic extracts are washed with water
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c1e30ccef6c34666a0b9cc4091476cfe
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06127576

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