Methanol → HCID 118432101, compound

HRID 2207952Notes

Reaction equation

HRID 2207952 reaction equation
C[O:2][C:3]([C:5]1[CH2:9][CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[Cl:16])[N:7]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)[N:6]=1)=[O:4].[OH-].[K+].CO>O>[Br:23][C:20]1[CH:21]=[CH:22][C:17]([N:7]2[CH:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[Cl:16])[CH2:9][C:5]([C:3]([OH:4])=[O:2])=[N:6]2)=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 118432002HCID 118432002, compound

Product 1

HCID 118432101HCID 118432101, compoundYield 105.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

1-(4-Bromo-phenyl)-5-(2-chloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester (5.3 g, 13.5 mmol) prepared in Step 3 and a solution of potassium hydroxide (2.0 g, 35.6 mmol) in distilled water (25.0 mL) were added to methanol (25.0 mL). The reaction mixture was stirred at 100° C. for 12 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 5.4 g of the titled compound as a white 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-82a9739038b94ec9a1bab3b6bbe3e6b3
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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