Sodium Chloride → HCID 22404755, compound

HRID 440695Notes

Reaction equation

HRID 440695 reaction equation
[C:1]([C:3]1[C:12]2[O:11][C:10]([CH3:14])([CH3:13])[CH:9]=[CH:8][C:7]=2[CH:6]=[CH:5][C:4]=1[F:15])#[N:2].[OH-:16].[K+].[Cl-].[Na+]>C(O)(C)(C)C>[CH3:14][C:10]1([CH3:13])[CH:9]=[CH:8][C:7]2[CH:6]=[CH:5][C:4]([F:15])=[C:3]([C:1]([NH2:2])=[O:16])[C:12]=2[O:11]1

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 14797Potassium HydroxideHCID 22404770HCID 22404770, compound

Product 1

HCID 22404755HCID 22404755, compoundYield 48.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A stirred solution of 5.0 grams (0.025 mole) of 8-cyano-2,2-dimethyl-7-fluoro-2H-1-benzopyran and 5.1 grams (0.091 mole) of potassium hydroxide in 60 mL of tert.-butanol was maintained at reflux for one hour and then poured into an aqueous solution saturated with sodium chloride. The mixture was extracted with ethyl acetate, and the extract was washed with an aqueous solution saturated with sodium chloride. The organic layer was dried with magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure, yielding 2.7 grams of 2,2-dimethyl-7-fluoro-2H-1-benzopyran-8-ylcarboxamide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. temperatureat reflux for one hour
  2. extractionThe mixture was extracted with ethyl acetate
  3. washthe extract was washed with an aqueous solution saturated with sodium chloride
  4. dry with materialThe organic layer was dried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-e8eaeacc6dff45a390e563bce295b6cb
Source dataset
uspto-grants-1996_05
Patent number
US05521147

Reaction notes

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