Hydrochloric Acid → 4'-Chloro-3,5-diethylbiphen-4-ylamine

HRID 341692Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 341692
Cl.C(OC(=O)[NH:8][C:9]1[C:14]([CH2:15][CH3:16])=[CH:13][C:12]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[CH:11][C:10]=1[CH2:24][CH3:25])(C)(C)C>CO>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:12]2[CH:11]=[C:10]([CH2:24][CH3:25])[C:9]([NH2:8])=[C:14]([CH2:15][CH3:16])[CH:13]=2)=[CH:18][CH:19]=1

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 59450514(4'-Chloro-3,5-diethylbiphen-4-yl)carbamic acid tert-butyl ester

Produkt 1

HCID 594504894'-Chloro-3,5-diethylbiphen-4-ylamineAusbeute 61,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Concentrated hydrochloric acid (22 ml) is added to a solution of (4′-chloro-3,5-diethylbiphen-4-yl)carbamic acid tert-butyl ester (22 g, 0.06 mol) in methanol (110 ml), and the reaction mixture is heated to 60° C. for 2 hours. The mixture is cooled to room temperature and most of the methanol is removed by evaporation under reduced pressure. The mixture is diluted with water, made basic by addition of 2N aqueous potassium hydroxide solution and extracted with ethyl acetate (3×200 ml). The organic extracts are combined and the solvents are removed under reduced pressure to give 4′-chloro-3,5-diethylbiphen-4-ylamine (9.6 g).

Aufarbeitung

  1. customis removed by evaporation under reduced pressure
  2. additionThe mixture is diluted with water
  3. additionmade basic by addition of 2N aqueous potassium hydroxide solution
  4. extractionextracted with ethyl acetate (3×200 ml)
  5. customthe solvents are removed under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-6b86e18ac0a845a59725c0cdefaa9012
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08895761B2

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