Water → 3,4-Dihydro-2H-1,4-benzoxazine

HRID 717772Notes

Reaction equation

HRID 717772 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH2:10][CH2:11]Br.C([O-])([O-])=O.[K+].[K+].O>C1COCC1>[O:8]1[CH2:11][CH2:10][NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 58012-AminophenolHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 5850963,4-Dihydro-2H-1,4-benzoxazineYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2-aminophenol (5 g, 45.87 mmol), 1,2-dibromoethane (4.3 g, 22.93 mmol), and K2CO3 (15.8 g, 114.67 mmol) in THF (30 mL) was heated at 100° C. for 16 h. After completion of reaction, water was added and extracted with EtOAc. The combined organic layers were dried over sodium sulfate and concentrated under reduced pressure. The reaction mixture was purified by column chromatography (using 100-200 mesh size silica, the desired product was eluted at 15% EtOAc in hexane) to obtained 1 g of desired product.

Workup

  1. additionwas added
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organic layers were dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe reaction mixture was purified by column chromatography (
  6. washthe desired product was eluted at 15% EtOAc in hexane)

Sources & evidence

ORD record
ord-d9451a9d04c844b781f03044f118198d
Source dataset
uspto-grants-2015_11
Patent number
US09193728B2

Reaction notes

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