Phenol → HCID 21432718, compound

HRID 2399108Notes

Reaction equation

HRID 2399108 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[N:8][C:7]([C:13]([OH:15])=[O:14])=[CH:6]2)[CH3:2].S(Cl)(Cl)=O.[C:20]1(O)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCCC1>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[N:8][C:7]([C:13]([O:15][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:14])=[CH:6]2)[CH3:2]

Participants

5

Reactant 3

HCID 996PhenolHCID 24386Thionyl ChlorideHCID 21432703HCID 21432703, compound

Product 1

HCID 21432718HCID 21432718, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 6-ethylcinnolin-3-yl carboxylic acid (0.606 g.) and thionyl chloride (30 ml.) was heated under reflux on a steam bath for 20 minutes. The resulting solution was evaporated under reduced pressure to give a yellow crystalline solid, to which was added a solution of phenol (1.13 g.) in dry tetrahydrofuran (20 ml.). The mixture was heated under reflux on a steam bath for 2 hours. The resulting solution was evaporated and the residue was washed by decantation with ether (2× 50 ml.). The residual brown oil was dissolved in ethyl acetate (50 ml.) and washed successively with 5% w/v aqueous sodium bicarbonate (10 ml.) and water (2× 10 ml.). The ethyl acetate solution was dried (MgSO4), filtered and evaporated, and the residual oil was applied to the top of a silica column (30 g. Kieselgel 60). Elution with a 50% v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.), and evaporation of the appropriate fractions, gave crude phenyl 6-ethylcinnolin-3-yl carboxylate. The product was recrystallised from aqueous ethanol, and then had m.p. 143°-145° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux on a steam bath for 20 minutes
  3. customThe resulting solution was evaporated under reduced pressure
  4. customto give a yellow crystalline solid
  5. temperatureThe mixture was heated
  6. temperatureunder reflux on a steam bath for 2 hours
  7. customThe resulting solution was evaporated
  8. washthe residue was washed by decantation with ether (2× 50 ml.)
  9. dissolutionThe residual brown oil was dissolved in ethyl acetate (50 ml.)
  10. washwashed successively with 5% w/v aqueous sodium bicarbonate (10 ml.) and water (2× 10 ml.)
  11. dry with materialThe ethyl acetate solution was dried (MgSO4)
  12. filtrationfiltered
  13. customevaporated
  14. washElution
  15. additionwith a 50% v/v mixture of ethyl acetate and petroleum ether (b.p. 60°-80° C.), and evaporation of the appropriate fractions

Sources & evidence

ORD record
ord-8a8388c71ee144eda1f23f12f4d86292
Source dataset
uspto-grants-1977_05
Patent number
US04027023

Reaction notes

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