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

HRID 253108

反応式

HRID 253108 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f679ff5520a7421c8a797bbebdd28209
出典データセット
uspto-grants-2011_01
特許番号
US07872009B2

関連ノート

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