Fluorobenzene → HCID 10752867, compound

HRID 1382199Notes

Reaction equation

HRID 1382199 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]2[C:7]([O:9][C:10](=[O:11])[C:3]=2[CH:2]=1)=[O:8].[Al+3].[Cl-].[Cl-].[Cl-].[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:7]([C:4]2[CH:5]=[CH:6][N:1]=[CH:2][C:3]=2[C:10]([OH:9])=[O:11])=[O:8])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 10008FluorobenzeneHCID 2783981H,3H-furo(3,4-c)pyridine-1,3-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10752867HCID 10752867, compound

Procedure

To a solution of pyridine-3,4-dicarboxylic anhydride (56.04 g, 0.38 mol) in 950 mL of fluorobenzene is added AlCl3 (126.67 g, 0.95 mol) over 45 min. from a powder addition funnel. The mixture is heated to reflux for 12 hours, then allowed to cool and quenched with ice water. Addition of a concentrated NaOH solution results in a solid precipitate which is filtered. The basic aqueous fraction of the biphasic filtrate is separated, washed with Et2O (3×150 mL), and acidified to pH 2.5 with concentrated HCl to generate a white solid which is collected by vacuum filtration. The solid is washed with several portions of hot MeOH to generate pure 3-(4-fluorobenzoyl)pyridine-4-carboxylic acid. M.P. 308.5° C. The combined methanolic filtrates are evaporated and recrystallized from MeOH to generate 4-(4-fluorobenzoyl)-pyridine-3-carboxylic acid. M.P. 231°-232.5° C.

Workup

  1. additionfrom a powder addition funnel
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 12 hours
  4. temperatureto cool
  5. customquenched with ice water
  6. additionAddition of a concentrated NaOH solution
  7. customresults in a solid precipitate which
  8. filtrationis filtered
  9. customThe basic aqueous fraction of the biphasic filtrate is separated
  10. washwashed with Et2O (3×150 mL)
  11. filtrationis collected by vacuum filtration
  12. washThe solid is washed with several portions of hot MeOH
  13. customThe combined methanolic filtrates are evaporated
  14. customrecrystallized from MeOH

Sources & evidence

ORD record
ord-ebb958b7bdc14905ab2e90d580d7fc79
Source dataset
uspto-grants-1989_02
Patent number
US04806535

Reaction notes

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