1,2-Dibromoethane → 2,3-Dihydro-1,4-dioxino[2,3-b]pyridine

HRID 1038594Notes

Reaction equation

HRID 1038594 reaction equation
[OH:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17]Br>CN(C=O)C>[O:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[O:1][CH2:17][CH2:16]1

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 178516237HCID 178516237, compound

Product 1

HCID 110079682,3-Dihydro-1,4-dioxino[2,3-b]pyridineYield 5.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2,3-Dihydroxypyridine (2.22 g, 20.0 mmol) was dissolved in N,N′-dimethylformamide (100 mL), and added potassium carbonate (5.52 g, 40.0 mmol) at room temperature. 5 minutes after, 1,2-dibromoethane (2.6 mL, 30.0 mmol) was added at the same temperature, and stirred at 90° C. overnight. The reaction solution was reverted to room temperature, filtered, and the obtained filtrate was concentrated in vacuo. Then, the obtained residue was added ethyl acetate. The suspension was filtered, washed ethyl acetate, and concentrated in vacuo. The title compound (157 mg (yield 5.7%)) was obtained as a colorless oil.

Workup

  1. customwas reverted to room temperature
  2. filtrationfiltered
  3. concentrationthe obtained filtrate was concentrated in vacuo
  4. additionThen, the obtained residue was added ethyl acetate
  5. filtrationThe suspension was filtered
  6. washwashed ethyl acetate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8717438d53b14ba0aa869f0a7d640caa
Source dataset
uspto-grants-2013_10
Patent number
US08551985B2

Reaction notes

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