Water → HCID 178467227, compound

HRID 1843659Notes

Reaction equation

HRID 1843659 reaction equation
[C:1]([C:3]1[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-:16])=[O:15])[CH:9]=2)=[N:5][NH:6][CH:7]=1)#[CH:2].O.FC(F)(F)C(O)=[O:21].C(OCC)C>O1CCOCC1>[N+:14]([C:10]1[CH:9]=[C:8]([C:4]2[C:3]([C:1](=[O:21])[CH3:2])=[CH:7][NH:6][N:5]=2)[CH:13]=[CH:12][CH:11]=1)([O-:16])=[O:15]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 6422Trifluoroacetic acidHCID 178437211HCID 178437211, compound

Product 1

HCID 178467227HCID 178467227, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 350 mg (1.6 mmol) of 4-ethynyl-3-(3-nitrophenyl)-1H-pyrazole in a mixture of 50 ml of dioxane and 0.5 ml (28 mmol) of water, 0.5 ml (6.5 mmol) of trifluoroacetic acid were added. The reaction was heated at 100° C. under stirring for 2 hours. The organic solvent was removed under reduced pressure and the residue partitioned between ethylacetate and aqueous sodium hydrogenocarbonate. The organic layer was then dried over sodium sulphate and evaporated to dryness, affording, after trituration with diethylether, 251 mg (68%) of the title compound.

Workup

  1. additionwere added
  2. customThe organic solvent was removed under reduced pressure
  3. customthe residue partitioned between ethylacetate and aqueous sodium hydrogenocarbonate
  4. dry with materialThe organic layer was then dried over sodium sulphate
  5. customevaporated to dryness
  6. customaffording

Sources & evidence

ORD record
ord-529703dd83434ad983b6dbd6980608f4
Source dataset
uspto-grants-2015_02
Patent number
US08946250B2

Reaction notes

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