Methanol → HCID 118431766, compound

HRID 2207934Notes

Reaction equation

HRID 2207934 reaction equation
C[O:2][C:3]([C:5]1[CH2:9][CH:8]([C:10]2[CH:11]=[N:12][C:13]([Br:16])=[CH:14][CH:15]=2)[N:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])[N:6]=1)=[O:4].[OH-].[K+].CO>O>[Br:16][C:13]1[N:12]=[CH:11][C:10]([CH:8]2[N:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])[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 118431723HCID 118431723, compound

Product 1

HCID 118431766HCID 118431766, compoundYield 70,318%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

5-(6-bromo-pyridin-3-yl)-1-(2-chloro-phenyl)-4,5-dihydro-1H-pyrazole-3-carboxylic acid methyl ester (650.0 mg, 1.7 mmol) prepared in Step 2 and a solution of potassium hydroxide (185.0 mg, 3.3 mmol) in distilled water (10.0 mL) were added to methanol (10.0 mL). The reaction mixture was stirred at 70° C. for 2 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 455.0 g 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-0a8e581fac8a48e0ab9548e712556a26
Source dataset
uspto-grants-2016_06
Patent number
US09376420B2

Reaction notes

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