Methanol → HCID 118431779, compound

HRID 2207939Notes

Reaction equation

HRID 2207939 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])=[C:12]([F:17])[CH:11]=2)[N:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[Cl:24])[N:6]=1)=[O:4].[OH-].[K+].CO>O>[Br:16][C:13]1[CH:14]=[CH:15][C:10]([CH:8]2[N:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[Cl:24])[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH2:9]2)=[CH:11][C:12]=1[F:17]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 118431700HCID 118431700, compound

Product 1

HCID 118431779HCID 118431779, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

5-(4-Bromo-3-fluoro-phenyl)-1-(2-chloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester (830.0 mg, 2.0 mmol) prepared in Step 3 and a solution of potassium hydroxide (226.0 mg, 4.0 mmol) in distilled water (10.0 mL) were added to methanol (10.0 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 820.0 mg of the titled compound as a pale 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-9cf683fa8cff4af2aa787c675a71088f
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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