Acetic Anhydride → HCID 14857385, compound

HRID 892599Notes

Reaction equation

HRID 892599 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]3[CH:15]=[N+:16]([O-])[CH:17]=[CH:18][CH:19]=3)[C:7]=2[CH:21]=1)#[N:2].C(OC(=O)C)(=[O:24])C>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[O:11][C:10]([CH3:13])([CH3:12])[CH2:9][CH:8]([C:14]3[C:15](=[O:24])[NH:16][CH:17]=[CH:18][CH:19]=3)[C:7]=2[CH:21]=1)#[N:2]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 54331976HCID 54331976, compound

Product 1

HCID 14857385HCID 14857385, compound

Procedure

400 mg of 3-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)pyridine N-oxide were dissolved in 10 ml of acetic anhydride and heated at reflux for 8 hours. After removal of the solvent by evaporation the residue was dissolved in ethanol and 15 mg of 80% (w/w) sodium hydride were added. After stirring for 30 minutes the mixture was evaporated and the residue was dissolved in a mixture of ethyl acetate and water. The aqueous phase was acidified with dilute hydrochloric acid, extracted with ethyl acetate, then made basic with sodium bicarbonate solution and re-extracted with ethyl acetate. The combined organic extracts were dried over sodium sulphate and evaporated. The residue was chromatographed on silica gel using 8% (v/v) methanol/ethyl acetate for the elution to give 310 mg of 3-(6-cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-2(1H)-pyridone of melting point 196°-197° C. after recrystallization from t-butyl methyl ether.

Workup

  1. temperatureheated
  2. temperatureat reflux for 8 hours
  3. customAfter removal of the solvent
  4. customby evaporation the residue
  5. dissolutionwas dissolved in ethanol
  6. addition15 mg of 80% (w/w) sodium hydride were added
  7. customwas evaporated
  8. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  9. extractionextracted with ethyl acetate
  10. extractionre-extracted with ethyl acetate
  11. dry with materialThe combined organic extracts were dried over sodium sulphate
  12. customevaporated
  13. customThe residue was chromatographed on silica gel using 8% (v/v) methanol/ethyl acetate for the elution

Sources & evidence

ORD record
ord-56989d848dc042ec816361dc876b6c51
Source dataset
uspto-grants-1992_06
Patent number
US05118694

Reaction notes

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