Réaction #5925

Équation de réaction

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

Rendement 72.8%

Solvants

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Lavagethe ethyl acetate layer is washed
2. 2
   Autredried
3. 3
   workup.DISTILLATIONdistilled
4. 4
   Autreto 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
   Températurethe mixture is refluxed for 2 hours
8. 8
   workup.DISTILLATIONacetone is distilled off
9. 9
   workup.ADDITIONTo the residue is added water
10. 10
    Autrethe precipitate is separated by filtration
11. 11
    Lavagewashed
12. 12
    Autredried
13. 13
    Autrerecrystallized from tetrahyrofuran

Mode opératoire

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%).

Source