Reaktion #64241

Reaktionsgleichung

sodium hydrogen carbonate

nitric acid

trans-N-acetyl-4-hydroxycyclohexylamine

acetic acid anhydride

→

title compound

trans-N-acetyl-4-nitroxycyclohexylamine

Lösungsmittel

—

ice water

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooled in an ice-bath to 0°-5° C.
2. 2
   Temperaturcooling at 0°-5° C
3. 3
   workup.STIRRINGThe reaction mixture is further stirred for 3 h at 0°-5° C.
4. 4
   ExtraktionAfter extraction with ethyl acetate
5. 5
   Trocknendrying of the organic phase with sodium sulphate
6. 6
   workup.DISTILLATIONdistilling off in a vacuum, there remain 17.8 g of crude product
7. 7
   SonstigeAfter recrystallisation from ethyl acetate, there

Vorschrift

28.3 ml (0.3 mol) acetic acid anhydride are mixed with 375 ml acetonitrile, cooled in an ice-bath to 0°-5° C. and 12.6 ml (0.3 mol) 100% nitric acid added dropwise. After 30 minutes, 15.7 g (0.1 mol) solid trans-N-acetyl-4-hydroxycyclohexylamine are added thereto with stirring and cooling at 0°-5° C. The reaction mixture is further stirred for 3 h at 0°-5° C. and subsequently allowed to flow carefully into a solution of 150 g (18 mol) sodium hydrogen carbonate in 500 ml ice water. After extraction with ethyl acetate, drying of the organic phase with sodium sulphate and distilling off in a vacuum, there remain 17.8 g of crude product. After recrystallisation from ethyl acetate, there are obtained 10.3 g of the title compound of the m.p. 146°-148° C., i.e. 50% of theory.

Quelle