Réaction #1553002

Équation de réaction

5-chloro-2-nitroaniline

2-(2-methoxy-ethoxy)-ethylamine

potassium carbonate

water

→

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

Solvants

N,N-dimethylacetamide

Conditions de réaction

Traitement

1. 1
   Extractionextracted with ethyl acetate
2. 2
   ExtractionThe organic extract
3. 3
   Lavagewas washed with brine
4. 4
   Autredried
5. 5
   Autreevaporated
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
   Lavageeluting first with 50% ethyl acetate/petroleum spirits (40-60° C.)
8. 8
   AutreEvaporation
9. 9
   Autreyielded
10. 10
    Autrean orange-red liquid, 1.1 g (45.8% yields)

Mode opératoire

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).

Source