Water → HCID 54136818, compound

HRID 1649785Notes

Reaction equation

HRID 1649785 reaction equation
[Br:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[H-].[Na+].Br[CH2:12][C:13]([O:15][CH3:16])=[O:14].O>C1COCC1>[Br:1][C:2]1[C:7]([O:8][CH2:12][C:13]([O:15][CH3:16])=[O:14])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 230702-Bromo-3-pyridinolHCID 24758Sodium hydrideHCID 60984Methyl bromoacetate

Product 1

HCID 54136818HCID 54136818, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-3-pyridinol (5 g) in THF (100 ml) at 0° was added sodium hydride (1 g, 80% suspension in oil). The mixture was stirred under nitrogen for 30 min and methyl bromoacetate (3.26 ml) was added dropwise. The mixture was then heated under reflux for 2 h, poured into water (300 ml) and extracted with ethyl acetate (2×250 ml). The combined organic extracts were dried and concentrated to give a solid which was triturated with ether to give the title compound as a white solid (4.5 g), m.p. 63°-64° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureunder reflux for 2 h
  3. extractionextracted with ethyl acetate (2×250 ml)
  4. customThe combined organic extracts were dried
  5. concentrationconcentrated
  6. customto give a solid which
  7. customwas triturated with ether

Sources & evidence

ORD record
ord-c031046e078e4e8caa565da6791e2d77
Source dataset
uspto-grants-1990_05
Patent number
US04921867

Reaction notes

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