2,4-Difluorophenylhydrazine hydrochloride → HCID 118432155, compound

HRID 2207941Notes

Reaction equation

HRID 2207941 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4](=O)[CH:5]=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=1.Cl.[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[NH:25][NH2:26]>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[CH2:5][CH:6]([C:7]2[CH:12]=[CH:11][C:10]([Br:13])=[CH:9][CH:8]=2)[N:25]([C:19]2[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=2[F:17])[N:26]=1)=[O:15]

Participants

4

Reactant 2

HCID 27333012,4-Difluorophenylhydrazine hydrochlorideHCID 57351455HCID 57351455, compound

Product 1

HCID 118432155HCID 118432155, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
125 °C

Procedure

4-(4-Bromo-phenyl)-2-oxo-3-butenoic acid methyl ester (50.0 g, 185.8 mmol) prepared in Step 2 of Preparation 17 and 2,4-difluorophenylhydrazine hydrochloride (36.9 g, 204.4 mmol) were added to acetic acid (600.0 mL). The reaction mixture was stirred at 125° C. for 3 hours, concentrated under reduced pressure, and then ethyl acetate was added thereto. The reaction mixture was washed with a saturated solution of sodium hydrogen carbonate, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 73.4 g of 5-(4-bromo-phenyl)-1-(2,4-difluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester as a yellow liquid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionethyl acetate was added
  3. washThe reaction mixture was washed with a saturated solution of sodium hydrogen carbonate
  4. dry with materialdried on anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d07d540949dd4aa7b4c4ecde16b508e6
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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