2-Chloroaniline hydrochloride → 8-Chloro-4-methylquinoline

HRID 1953455

Reaktionsgleichung

Reaktionsgleichung von HRID 1953455
Cl.[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[CH:6][C:4]=1[NH2:5].CO[CH2:12][CH2:13][C:14](OC)(OC)[CH3:15]>[Cl-].[Zn+2].[Cl-].C(O)C>[Cl:2][C:3]1[CH:9]=[CH:8][CH:7]=[C:6]2[C:4]=1[N:5]=[CH:12][CH:13]=[C:14]2[CH3:15]

Komponenten

5

Edukt 2

HCID 672982-Chloroaniline hydrochlorideHCID 810844-Methoxybutan-2-one-dimethylacetal

Produkt 1

HCID 2807468-Chloro-4-methylquinoline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Commercially available 2-chloroaniline (200 g, 1.56 mol) was dissolved in 600 ml ethanol, and dry HCl gas was bubbled through for 10 minutes to give 2-chloroaniline hydrochloride. A new flask was charged with 2-chloroaniline hydrochloride (130 g, 0.793 mol), ferric chloride hexahydrate (25.7 g, 0.095 mol), anhydrous zinc chloride (10.9 g, 0.0799 mol) and 500 ml 2B ethanol. The mixture was heated to 60° C. for 10 minutes and 1,3,3-trimethoxy butane was added dropwise over a period of one hour. The mixture was then refluxed for two hours and allowed to stand overnight at room temperature. Most of the alcohol was removed by distillation and the residue was made alkaline with 25% sodium hydroxide solution. The reaction was cooled, filtered, and the filter pad washed with toluene. The toluene was concentrated to dryness. The product was recrystallized from dichloromethane/pentane to obtained a spectroscopically pure sample (mp: 110° C., 37.0 g, 25% overall yield).

Aufarbeitung

  1. temperatureThe mixture was then refluxed for two hours
  2. customMost of the alcohol was removed by distillation
  3. temperatureThe reaction was cooled
  4. filtrationfiltered
  5. washthe filter pad washed with toluene
  6. concentrationThe toluene was concentrated to dryness
  7. customThe product was recrystallized from dichloromethane/pentane
  8. customto obtained
  9. customa spectroscopically pure sample (mp: 110° C., 37.0 g, 25% overall yield)

Quellen und Nachweise

ORD-Eintrag
ord-2ad0e15a83d34a87a7d0ebbd602e5366
Quelldatensatz
uspto-grants-2000_09
Patentnummer
US06117884

Verknüpfte Notizen

Wird geladen…