Reaktion #1553002

Reaktionsgleichung

5-chloro-2-nitroaniline

2-(2-methoxy-ethoxy)-ethylamine

potassium carbonate

water

→

N1-[2-(2-methoxy-ethoxy)-ethyl]-4-nitro-benzene-1,3-diamine

Lösungsmittel

N,N-dimethylacetamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with ethyl acetate
2. 2
   ExtraktionThe organic extract
3. 3
   Waschenwas washed with brine
4. 4
   Sonstigedried
5. 5
   Sonstigeevaporated
6. 6
   FiltrationThe resulting orange yellow oil was subjected to a silica gel filtration on a 5 cm×6 cm silica gel plug
7. 7
   Wascheneluting first with 50% ethyl acetate/petroleum spirits (40-60° C.)
8. 8
   SonstigeEvaporation
9. 9
   Sonstigeyielded
10. 10
    Sonstigean orange-red liquid, 1.1 g (45.8% yields)

Vorschrift

A mixture of 5-chloro-2-nitroaniline (1.6 g, 9.3 mmol), 2-(2-methoxy-ethoxy)-ethylamine (2.0 g, 16.8 mmol) and anhydrous potassium carbonate (1.38 g, 10 mmol) in N,N-dimethylacetamide (3 ml) was stirred at 120° C. under nitrogen for 3 days. Sample NMR analysis showed 80% conversion of the starting material. The resultant mixture was then cooled to room temperature, poured into cold water (30 ml) and extracted with ethyl acetate. The organic extract was washed with brine, dried and evaporated. The resulting orange yellow oil was subjected to a silica gel filtration on a 5 cm×6 cm silica gel plug, eluting first with 50% ethyl acetate/petroleum spirits (40-60° C.), followed by 100% ethyl acetate. Evaporation yielded an orange-red liquid, 1.1 g (45.8% yields).

Quelle