Methanol → HCID 118432180, compound

HRID 2207942Notes

Reaction equation

HRID 2207942 reaction equation
C[O:2][C:3]([C:5]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][C:13]([Br:16])=[CH:12][CH:11]=2)[N:7]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=2[F:24])[N:6]=1)=[O:4].[OH-].[K+].CO>O>[Br:16][C:13]1[CH:12]=[CH:11][C:10]([CH:8]2[N:7]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[F:24])[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH2:9]2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 118432155HCID 118432155, compound

Product 1

HCID 118432180HCID 118432180, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

The 5-(4-bromo-phenyl)-1-(2,4-difluoro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester in the form of a yellow liquid (73.4 g, 185.8 mmol) and a solution of potassium hydroxide (20.9 g, 371.6 mmol) in distilled water (400.0 mL) were added to methanol (400.0 mL). The reaction mixture was stirred at 70° C. for 4 hours and then concentrated under reduced pressure to discard methanol. The resulting residue was washed with diethyl ether, acidified by a 1N hydrochloric acid solution, and then extracted with ethyl acetate. The extract was washed with distilled water and brine, dried on anhydrous magnesium sulfate, and then concentrated under reduced pressure to give 70.0 g of the titled compound as a yellow solid.

Workup

  1. concentrationconcentrated under reduced pressure
  2. washThe resulting residue was washed with diethyl ether
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with distilled water and brine
  5. dry with materialdried on anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d0ed6fdd56574578908e54a13e78cf1c
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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