Sulfuric Acid → HCID 13958724, compound

HRID 255980Notes

Reaction equation

HRID 255980 reaction equation
S(=O)(=O)(O)O.[N+:6]([O-:9])([O-])=[O:7].[K+].[F:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18]1[CH:23]=[C:22]([CH3:24])[N:21]=[C:20]([CH3:25])[CH:19]=1.[OH-].[NH4+]>>[F:11][C:12]1[CH:17]=[CH:16][C:15]([N+:6]([O-:9])=[O:7])=[CH:14][C:13]=1[C:18]1[CH:19]=[C:20]([CH3:25])[N:21]=[C:22]([CH3:24])[CH:23]=1

Participants

5

Reactant 4

HCID 1118Sulfuric Acid2×HCID 14923Ammonium HydroxideHCID 24434Potassium NitrateHCID 13958722HCID 13958722, compound

Product 1

HCID 13958724HCID 13958724, compoundYield 84%

Procedure

To 55 ml of concentrated sulphuric acid cooled in a salt-ice bath to about -10° to -15° C. was added 10.1 g of potassium nitrate over a 5 minute period. The mixture was allowed to stir for 10 minutes and then to it was added dropwise over a 30 minute period 18.5 g of 4-(2-fluorophenyl)-2,6-dimethylpyridine whereupon a gummy solid separated and a viscous slurry was obtained, the reaction temperature rising to about 0° C. In order to facilitate stirring, another 50 ml portion of concentrated sulphuric acid was added dropwise over a 15 minute period and the resulting mixture was stirred in the salt-ice bath and then stirred for a period of about 5 hours while allowing the temperature of the reaction mixture to rise to room temperature. The reaction mixture was poured onto a large excess of ice and the mixture was neutralized by adding aqueous ammonium hydroxide solution. The resulting light yellow fluffy precipitate was collected, washed with water and air dried. The solid was then dissolved in 300 ml of chloroform, the solution treated with decolorizing charcoal and filtered. The filtrate was concentrated on a rotary evaporator and the residue was slurred with 200 ml of 1:1 ether-n-hexane, the mixture filtered and the collected solid dried at 70°-75° C. to yield 18.67 g (84%) of 4-(2-fluoro-5-nitrophenyl)-2,6-dimethylpyridine, m.p. 169°-171° C.

Workup

  1. customseparated
  2. customa viscous slurry was obtained
  3. customrising to about 0° C
  4. stirringIn order to facilitate stirring
  5. stirringstirred for a period of about 5 hours
  6. customto rise to room temperature
  7. additionThe reaction mixture was poured onto a large excess of ice
  8. customThe resulting light yellow fluffy precipitate was collected
  9. washwashed with water and air
  10. customdried
  11. dissolutionThe solid was then dissolved in 300 ml of chloroform
  12. additionthe solution treated with decolorizing charcoal
  13. filtrationfiltered
  14. concentrationThe filtrate was concentrated on a rotary evaporator
  15. filtrationthe mixture filtered
  16. customthe collected solid dried at 70°-75° C.

Sources & evidence

ORD record
ord-e0b25e4d8e6c4440936daec148f68c58
Source dataset
uspto-grants-1987_10
Patent number
US04699984

Reaction notes

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