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Ethyl Acetate → 2-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine

HRID 234899
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HRID 234899 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=1[OH:12].C(OCC)(=O)C.C(=O)([O-])O.[Na+].Br[CH:25]([CH2:29][CH3:30])[C:26](Br)=[O:27]>O>[CH2:29]([CH:25]1[C:26](=[O:27])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]([O:10][CH3:11])=[O:9])=[CH:4][C:3]=2[O:12]1)[CH3:30]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 1172932-Bromobutanoyl bromideHCID 516892Sodium BicarbonateHCID 7020619Benzoic acid, 4-amino-3-hydroxy-, methyl ester

생성물 1

HCID 233531642-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine수율 87%

시약·촉매·용매 1

HCID 962
Water
용매

실험 절차

To a solution of 2-amino-5-methoxycarbonylphenol [Tetrahedron, 46(15), 5177-5186 (1990)] (9.80 g) in a mixed solvent of ethyl acetate (200 ml) and water (200 ml) were added sodium hydrogen carbonate (7.30 g) and 2-bromobutyryl bromide (13.70 g) and the mixture was stirred at room temperature for 10 minutes. The organic layer was separated and the solvent was distilled off under reduced pressure. The resulting residue was dissolved in dimethylformamide (500 ml), to the solution was added potassium carbonate (8.90 g) and the mixture was stirred at room temperature for a day. The reaction solution was poured into water to give precipitates, which were taken by filtration and dried to give 2-ethyl-7-methoxycarbonyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazine (12.0 g).

후처리

  1. customThe organic layer was separated
  2. distillationthe solvent was distilled off under reduced pressure
  3. dissolutionThe resulting residue was dissolved in dimethylformamide (500 ml), to the solution
  4. additionwas added potassium carbonate (8.90 g)
  5. stirringthe mixture was stirred at room temperature for a day
  6. additionThe reaction solution was poured into water
  7. customto give
  8. customprecipitates
  9. filtrationwhich were taken by filtration
  10. customdried

출처 및 근거

ORD 기록
ord-3f799eee7bde4f37b8c1e0686a48f40d
출처 데이터셋
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05597820

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