Pyridine → 3-Bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylic acid

HRID 544175Notes

Reaction equation

HRID 544175 reaction equation
[Br:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:4][C:3]=1[C:15]([O:17]C)=[O:16].[I-].[Na+].N1C=CC=CC=1>C(C(C)=O)C.O>[Br:1][C:2]1[C:7](=[O:8])[CH:6]=[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:4][C:3]=1[C:15]([OH:17])=[O:16]

Participants

6

Reactant 3

HCID 1049PyridineHCID 5238Sodium IodideHCID 15578421Methyl 3-bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylate

Product 1

HCID 155783753-Bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

Methyl 3-bromo-4-oxo-6-phenyl-4H-pyran-2-carboxylate (587 g) was added to a stirred solution of dry sodium iodide (315 g) in dry methyl ethyl ketone (8 l). The solution was heated under reflux for 5 minutes, then pyridine (152 ml) was added and heating was continued for 31/2 hours. The mixture was cooled, the solid product was dissolved in water (2 l) and the solution was washed with dichloromethane and filtered. The filtrate was diluted to 10 l and acidified with 5M hydrochloric acid (760 ml) to precipitate the title product (mp 247° C. with decomposition).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 5 minutes
  3. temperatureheating
  4. custom2 hours
  5. temperatureThe mixture was cooled
  6. washthe solution was washed with dichloromethane
  7. filtrationfiltered
  8. additionThe filtrate was diluted to 10 l
  9. customto precipitate the title product (mp 247° C. with decomposition)

Sources & evidence

ORD record
ord-6df548510ad3459dbe2246e7fc7ce235
Source dataset
uspto-grants-1984_05
Patent number
US04448787

Reaction notes

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