2-Aminophenol → Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

HRID 253108

반응식

HRID 253108 반응식
Br[CH:2]([CH2:8]Br)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[OH:17].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[O:17]1[CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH2:8][NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]1=2

참가 물질

5

반응물 3

HCID 58012-AminophenolHCID 11430Potassium CarbonateHCID 97945Ethyl 2,3-dibromopropionate

생성물 1

HCID 31090Ethyl 3,4-dihydro-2H-1,4-benzoxazine-2-carboxylate

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To a solution of ethyl 2,3-dibromopropionate (8.05 g, 31.0 mmol, Aldrich) in acetone (35 mL) was added o-aminophenol (3.38 g. 31.0 mmol) and potassium carbonate (5.1 g, 36.9 mmol). The reaction mixture was stirred at reflux under a water condenser for 18 h. Upon cooling to room temperature, the reaction was concentrated in vacuo, and the residue was taken up in water (50 mL) and the product was extracted using EtOAc (3×75 mL). The organic fractions were combined, washed with saturated brine (15 mL), dried over sodium sulfate, and concentrated. Purification of the product by flash column chromatography (30% EtOAc/hexane) afforded the title compound as a yellow oil. MS m/z: 208 (M+1).

후처리

  1. temperatureat reflux under a water condenser for 18 h
  2. concentrationthe reaction was concentrated in vacuo
  3. extractionthe product was extracted
  4. washwashed with saturated brine (15 mL)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customPurification of the product by flash column chromatography (30% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-f679ff5520a7421c8a797bbebdd28209
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872009B2

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