반응 #5925

반응 방정식

α-bromo-4-chlorophenylacetyl chloride

1-amino-2-naphthol

N,N-dimethylaniline

tetrahydrofuran

→

3-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]oxazin-2(3H)-one

수율 72.8%

용매

ethyl acetate

반응 조건

후처리

1. 1
   세척the ethyl acetate layer is washed
2. 2
   기타dried
3. 3
   workup.DISTILLATIONdistilled
4. 4
   기타to remove the solvent
5. 5
   workup.DISSOLUTIONThe resulting oil is dissolved in acetone (500 ml)
6. 6
   workup.ADDITIONis added potassium carbonate (40.8 g)
7. 7
   온도the mixture is refluxed for 2 hours
8. 8
   workup.DISTILLATIONacetone is distilled off
9. 9
   workup.ADDITIONTo the residue is added water
10. 10
    기타the precipitate is separated by filtration
11. 11
    세척washed
12. 12
    기타dried
13. 13
    기타recrystallized from tetrahyrofuran

실험 절차

To a mixture of 1-amino-2-naphthol (9.4 g), N,N-dimethylaniline (17.87 g) and tetrahydrofuran (160 ml) is added dropwise α-bromo-4-chlorophenylacetyl chloride (18.97 g) under ice cooling, and the mixture is stirred for one hour. To the reaction mixture is added ethyl acetate, and the ethyl acetate layer is washed, dried and distilled to remove the solvent. The resulting oil is dissolved in acetone (500 ml) and thereto is added potassium carbonate (40.8 g), and the mixture is refluxed for 2 hours, and acetone is distilled off. To the residue is added water, and the precipitate is separated by filtration, washed, dried and recrystallized from tetrahyrofuran to give 3-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]oxazin-2(3H)-one (13.29 g, yield 72.8%).

출처