N,N-Dimethylaniline → 1H-naphth(2,1-b)(1,4)oxazin-2(3H)-one

HRID 1439857

반응식

HRID 1439857 반응식
[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.[O:22]1CC[CH2:24][CH2:23]1.ClCC(Cl)=O>C(OCC)(=O)C>[NH:1]1[C:23](=[O:22])[CH2:24][O:12][C:3]2[CH:4]=[CH:5][C:6]3[C:11]([C:2]1=2)=[CH:10][CH:9]=[CH:8][CH:7]=3

참가 물질

6

반응물 4

HCID 949N,N-DimethylanilineHCID 6577Chloroacetyl chlorideHCID 8028TetrahydrofuranHCID 145351-Amino-2-naphthol

생성물 1

HCID 846651H-naphth(2,1-b)(1,4)oxazin-2(3H)-one

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

To a mixture of 1-amino-2-naphthol (16.9 g), N,N-dimethylaniline (19.3 g) and tetrahydrofuran (200 ml) is added dropwise chloroacetyl chloride under ice cooling, and the mixture is stirred at the same temperature 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 (75 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 1H-naphtho[2,1-b][1,4]oxazin-2(3H)-one (13.1 g). M.p. 219°-220.5° C.

후처리

  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 (75 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

출처 및 근거

ORD 기록
ord-612c7cbaea9e4c7b8d1d681e848412e0
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05496815

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