Allyl bromide → HCID 53964332, compound

HRID 443440Notes

Reaction equation

HRID 443440 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][N:6]=1)=[O:4].[H-].[Na+].[CH2:14](Br)[CH:15]=[CH2:16]>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:16][CH:15]=[CH2:14])=[CH:7][N:6]=1)=[O:4]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 4715126Methyl 5-hydroxypyridine-2-carboxylate

Product 1

HCID 53964332HCID 53964332, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

4.7 g of 5-hydroxy-2-pyridinecarboxylic acid methyl ester is added to a stirred suspension of 1.30 g of sodium hydride (57% mineral oil dispersion) in 10 ml of dimethylformamide at room temperature while maintaining a nitrogen atmosphere. The mixture is stirred for 30 minutes and then is added a solution of 3.90 g of allyl bromide in 20 ml of dimethylformamide. The mixture is heated to 100° and maintained at 100° for 5 hours. Then the mixture is cooled, filtered and the filtrate evaporated to a residue. The residue is partitioned between water and methylene chloride, the layers are separated and the water layer is extracted with methylene chloride. The methylene layer is combined with the methylene extract, dried over anhydrous sodium sulfate and filtered. The filtrate is evaporated and the residue is distilled to yield 5-allyloxy-2-pyridinecarboxylic acid methyl ester boiling at 124°-130°/0.15 mm/Hg.

Workup

  1. temperaturewhile maintaining a nitrogen atmosphere
  2. temperatureThe mixture is heated to 100°
  3. temperaturemaintained at 100° for 5 hours
  4. temperatureThen the mixture is cooled
  5. filtrationfiltered
  6. customthe filtrate evaporated to a residue
  7. customThe residue is partitioned between water and methylene chloride
  8. customthe layers are separated
  9. extractionthe water layer is extracted with methylene chloride
  10. extractionextract
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customThe filtrate is evaporated
  14. distillationthe residue is distilled

Sources & evidence

ORD record
ord-0654b86e1cbb42878399075e78da6664
Source dataset
uspto-grants-1981_04
Patent number
US04260620

Reaction notes

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