Hydrochloric Acid → HCID 10014744, compound

HRID 1081323Notes

Reaction equation

HRID 1081323 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]2[C:7]([O:9][C:10](=[O:11])[C:2]=12)=[O:8].[Cl-].[Al+3].[Cl-].[Cl-].Cl.C(=O)([O-])[O-].[K+].[K+].[F:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:7]([C:3]2[C:2]([C:10]([OH:9])=[O:11])=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:8])=[CH:26][CH:25]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 10008FluorobenzeneHCID 11430Potassium CarbonateHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10014744HCID 10014744, compound

Procedure

To a mixture of 2,3-pyridinedicarboxylic anhydride (16.5 g) and fluorobenzene (120 ml) was added, while stirring at room temperature, anhydrous aluminum chloride (23.1 g). The reaction mixture was stirred for 3 hours under reflux, which was cooled and poured into a mixture of hydrochloric acid and ice-water. This mixture was made to be pH 2-3 with an aqueous solution of potassium carbonate, which was subjected to extraction with ethyl acetate. The extract solution was washed with water and dried, then the solvent was distilled off to leave 3-(4-fluorobenzoyl)-2-pyridinecarboxylic acid as colorless crystals (11.0 g). m.p.152°-153° C. (recrystallized from methanol-ethyl acetate)

Workup

  1. additionwas added
  2. stirringThe reaction mixture was stirred for 3 hours
  3. temperatureunder reflux
  4. temperaturewhich was cooled
  5. extractionwas subjected to extraction with ethyl acetate
  6. washThe extract solution was washed with water
  7. customdried
  8. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-400f82ca0ad44138b02e14b59874f8fa
Source dataset
uspto-grants-1996_12
Patent number
US05585385

Reaction notes

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