반응 #1463878

반응 방정식

triethylamine

p-fluoronitrobenzene

N-methylallylamine

N-methyl-2-pyrrolidinone

→

N-allyl-N-methyl-4-nitroaniline

수율 96.0%

용매

water

반응 조건

후처리

1. 1
   온도was heated to 60°-70° C. for 5 hours in an oil bath
2. 2
   추출extracted twice with ether
3. 3
   세척The extracts were washed with distilled water and brine solution
4. 4
   건조dried over potassium carbonate
5. 5
   농축concentrated to an oil
6. 6
   workup.DISTILLATIONThe oil was distilled via Kugelrohr apparatus (forecut
7. 7
   기타taken up to 90° C.
8. 8
   기타discarded, 110°-125° C.

실험 절차

A mixture of p-fluoronitrobenzene (2.8 g, 20 mmol), N-methylallylamine (2.10 g, 30 mmol), triethylamine (2.0 g, 20 mmol), and N-methyl-2-pyrrolidinone (NMP) (20 ml) was heated to 60°-70° C. for 5 hours in an oil bath. The mixture was diluted with distilled water (100 ml) and extracted twice with ether. The extracts were washed with distilled water and brine solution, dried over potassium carbonate and concentrated to an oil. The oil was distilled via Kugelrohr apparatus (forecut taken up to 90° C. discarded, 110°-125° C., 0.1 mm Hg) to give 3.70 g (96%) N-allyl-N-methyl-4-nitroaniline. As is, this material failed to undergo clean hydrosilation, possibly due to residual N-methyl-2-pyrrolidinone present. The remaining material was chromatographed on silica with hexane-ethyl acetate (10:1) and distilled again via Kugelrohr apparatus to give a yellow oil that underwent clean hydrosilation.

출처