Sodium Bicarbonate → HCID 22020936, compound

HRID 1793310Notes

Reaction equation

HRID 1793310 reaction equation
Br[CH:2]([CH2:12][Br:13])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][N:8]=[CH:7][C:6]=1[OH:11].C([O-])(O)=O.[Na+]>C(O)C>[Br:13][CH2:12][CH:2]1[O:11][C:6]2[CH:7]=[N:8][CH:9]=[CH:10][C:5]=2[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 220209444-(2,3-Dibromopropoxy)pyridin-3-ol

Product 1

HCID 22020936HCID 22020936, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of intermediate (9) (0.0097 mol) in ethanol (50 ml) was stirred and refluxed overnight. NaHCO3 (0.0097 mol) was added and the resulting reaction mixture was stirred and refluxed overnight. The solvent was evaporated. The residue was washed with water and extracted with DCM. The organic layer was dried, filtered and the solvent was evaporated. The residue was purified by open column chromatography (eluent: hexane/ethyl acetate (3/2)). The pure fractions were collected and the solvent was evaporated, yielding 1.51 g of (±)-3-(bromomethyl)-2,3-dihydro-1,4-dioxino[2,3-c]pyridine (intermediate 10).

Workup

  1. temperaturerefluxed overnight
  2. customthe resulting reaction mixture
  3. temperaturerefluxed overnight
  4. customThe solvent was evaporated
  5. washThe residue was washed with water
  6. extractionextracted with DCM
  7. customThe organic layer was dried
  8. filtrationfiltered
  9. customthe solvent was evaporated
  10. customThe residue was purified by open column chromatography (eluent: hexane/ethyl acetate (3/2))
  11. customThe pure fractions were collected
  12. customthe solvent was evaporated

Sources & evidence

ORD record
ord-4a1d3a61ac65482faaad1b568ca78b0e
Source dataset
uspto-grants-2006_07
Patent number
US07081453B2

Reaction notes

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