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

HRID 5829

Reaktionsgleichung

Reaktionsgleichung von HRID 5829
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[OH:12].CN(C)C1C=CC=CC=1.O1CCCC1.Br[CH:28]([C:32]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=1)[C:29](Cl)=[O:30]>C(OCC)(=O)C>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH:28]2[O:12][C:3]3[CH:4]=[CH:5][C:6]4[C:11]([C:2]=3[NH:1][C:29]2=[O:30])=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:33][CH:34]=1

Komponenten

6

Edukt 4

HCID 949N,N-DimethylanilineHCID 8028TetrahydrofuranHCID 145351-Amino-2-naphtholHCID 12575778Bromo-4-chlorophenylacetyl chloride

Produkt 1

HCID 189844423-(4-chlorophenyl)-1H-naphtho[2,1-b][1,4]oxazin-2(3H)-oneAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  1. washthe ethyl acetate layer is washed
  2. customdried
  3. distillationdistilled
  4. customto remove the solvent
  5. dissolutionThe resulting oil is dissolved in acetone (500 ml)
  6. additionis added potassium carbonate (40.8 g)
  7. temperaturethe mixture is refluxed for 2 hours
  8. distillationacetone is distilled off
  9. additionTo the residue is added water
  10. customthe precipitate is separated by filtration
  11. washwashed
  12. customdried
  13. customrecrystallized from tetrahyrofuran

Quellen und Nachweise

ORD-Eintrag
ord-d364fc4681ef4cc7a031ee2d8b2fe643
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246929

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