Potassium Carbonate → HCID 15725733, compound

HRID 265413Notes

Reaction equation

HRID 265413 reaction equation
[C:1]1([C:7]2[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[CH:10][NH:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([O:28]CC)=[O:27].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC.C(O)C.[OH-].[Na+]>[C:1]1([C:7]2[C:11]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[CH:10][N:9]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]([OH:28])=[O:27])[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 264813Ethyl 8-bromooctanoateHCID 3017433,4-Diphenylpyrazole

Product 1

HCID 15725733HCID 15725733, compoundYield 13.3%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6569Methyl Ethyl KetoneSolventHCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3,4-diphenylpyrazole (2.2 g), ethyl 8-bromooctanoate (5.5 g) and potassium carbonate (3.7 g) in dry butanone (50 ml) was heated at reflux temperature for 44 hours. The mixture was filtered and the filtrate evaporated to an oil which was chromatographed on silica gel (hexane/ethyl acetate). The oil obtained was heated at reflux temperature in a mixture of ethanol and 2N sodium hydroxide (1:1) for 1 hour. The ethanol was evaporated and the aqueous residue was acidified with dilute hydrochloric acid to pH 3, extracted with dichloromethane, dried over magnesium sulphate and evaporated to a solid. This was recrystallised from dichloromethane/ether to give 8-(3,4-diphenylpyrazol-1-yl)octanoic acid (0.48 g, 13%) as colourless crystals, m.p. 114°-5° C. Found: C, 76.02; H, 7.25; N, 7.63%; C23H26N2O2 requires: C, 76.21; H, 7.23; N. 7.73%

Workup

  1. temperaturewas heated
  2. temperatureat reflux temperature for 44 hours
  3. filtrationThe mixture was filtered
  4. customthe filtrate evaporated to an oil which
  5. customwas chromatographed on silica gel (hexane/ethyl acetate)
  6. customThe oil obtained
  7. temperaturewas heated
  8. temperatureat reflux temperature
  9. customThe ethanol was evaporated
  10. extractionextracted with dichloromethane
  11. dry with materialdried over magnesium sulphate
  12. customevaporated to a solid
  13. customThis was recrystallised from dichloromethane/ether

Sources & evidence

ORD record
ord-86463d33c19a445cbf8d6741f8b6aa7a
Source dataset
uspto-grants-1997_07
Patent number
US05648373

Reaction notes

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