Potassium Carbonate → HCID 178526587, compound

HRID 1427674Notes

Reaction equation

HRID 1427674 reaction equation
C([N:4]1[CH:8]=[CH:7][C:6]([OH:9])=[N:5]1)(=O)C.[N+:10]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15]Br)([O-:12])=[O:11].C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[N+:10]([C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH2:15][O:9][C:6]1[CH:7]=[CH:8][NH:4][N:5]=1)([O-:12])=[O:11]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 77569alpha-Bromo-2-nitrotolueneHCID 178473861HCID 178473861, compound

Product 1

HCID 178526587HCID 178526587, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension of 1-acetyl-3-hydroxy-pyrazole (3.4 g, 27.0 mmol), 2-nitrobenzyl bromide (5.9 g, 27.3 mmol) and K2CO3 (4.0 g, 28.9 mmol) in 75 mL of 2-butanone was heated to reflux for 90 min. After cooling to room temperature, the precipitated salts were filtered off and rinsed with tert-butyl methyl ether (TBME). The filtrate was then concentrated under reduced pressure (50 mbar) and redissolved in a mixture of tetrahydrofuran (THF) and methanol (MeOH) (3:2, 50 mL). 2 mL of a 10% NaOH solution were added and the solution was stirred 60 min at ambient temperature. Then, all volatiles were removed under reduced pressure (50 mL). The residue was diluted with 20 mL of H2O and 30 mL of ethyl acetate (EtOAc). The aqueous phase was extracted with EtOAc (2×20 mL). The combined org. layers were washed with water and brine (both 30 mL) and dried over Na2SO4. The crude product was obtained after evaporation of all volatiles and recrystallised from dichloromethane (15 mL) to give the product as yellowish crystals (5.0 g, 22.8 mmol, 84%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 90 min
  3. filtrationthe precipitated salts were filtered off
  4. washrinsed with tert-butyl methyl ether (TBME)
  5. concentrationThe filtrate was then concentrated under reduced pressure (50 mbar)
  6. dissolutionredissolved in a mixture of tetrahydrofuran (THF) and methanol (MeOH) (3:2, 50 mL)
  7. addition2 mL of a 10% NaOH solution were added
  8. customThen, all volatiles were removed under reduced pressure (50 mL)
  9. additionThe residue was diluted with 20 mL of H2O and 30 mL of ethyl acetate (EtOAc)
  10. extractionThe aqueous phase was extracted with EtOAc (2×20 mL)
  11. washlayers were washed with water and brine (both 30 mL) and
  12. dry with materialdried over Na2SO4
  13. customThe crude product was obtained
  14. customafter evaporation of all volatiles
  15. customrecrystallised from dichloromethane (15 mL)

Sources & evidence

ORD record
ord-477c2245b2a5409cb51a006769f0fa1b
Source dataset
uspto-grants-2015_01
Patent number
US08933246B2

Reaction notes

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