Fluorobenzene → HCID 10014744, compound

HRID 1382191Notes

Reaction equation

HRID 1382191 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].[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:3]2[C:2]([C:10]([OH:9])=[O:11])=[N:1][CH:6]=[CH:5][CH:4]=2)=[O:8])=[CH:19][CH:18]=1

Participants

4

Reactant 3

HCID 10008FluorobenzeneHCID 69688Furo[3,4-b]pyridine-5,7-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10014744HCID 10014744, compound

Procedure

A mixture of 2,3-pyridinedicarboxylic anhydride (9.0 g, 60.36 mmol) in 75 mL of fluorobenzene is warmed and stirred mechanically while AlCl3 (17.7 g, 0.132 mol) is added portionwise from a powder addition funnel over 20 m. The resulting mixture is heated to reflux for 24 hours, then allowed to cool and the excess fluorobenzene decanted. Quenching of the residue with ice water and 5% aqueous HCl generates a solid which is filtered and washed with hot H2O. The combined filtrates are evaporated to a final volume of ca. 250 mL, then heated to boiling and treated with a hot solution of 15% aqueous CuSO4 solution to precipitate a blue solid. The suspension is filtered and the resulting solid resuspended in H2O (75 mL) and treated with a stream of H2S gas until the initial blue color of the suspension subsides and is replaced by a black suspension. The solid is filtered with the aid of Celite and the filtrate evaporated to produce a tan solid which is recrystallized from H2O to obtain 3-(4-fluorobenzoyl)pyridine-2-carboxylic acid. M.P. 153.5°-155° C.

Workup

  1. temperatureis warmed
  2. additionis added portionwise from a powder addition funnel over 20 m
  3. temperatureThe resulting mixture is heated
  4. temperatureto reflux for 24 hours
  5. temperatureto cool
  6. customthe excess fluorobenzene decanted
  7. customQuenching of the residue with ice water and 5% aqueous HCl
  8. filtrationis filtered
  9. washwashed with hot H2O
  10. customThe combined filtrates are evaporated to a final volume of ca. 250 mL
  11. temperatureheated
  12. additiontreated with a hot solution of 15% aqueous CuSO4 solution
  13. customto precipitate a blue solid
  14. filtrationThe suspension is filtered
  15. additiontreated with a stream of H2S gas until the initial blue color of the suspension subsides
  16. filtrationThe solid is filtered with the aid of Celite
  17. customthe filtrate evaporated
  18. customto produce a tan solid which
  19. customis recrystallized from H2O

Sources & evidence

ORD record
ord-61525a305b37429ab583bb18d983457f
Source dataset
uspto-grants-1989_02
Patent number
US04806535

Reaction notes

Loading…