Tetrahydrofuran → 1-(3,5-dichloropyridin-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acid

HRID 453068Notes

Reaction equation

HRID 453068 reaction equation
[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([O:16]C)=[O:15])=[CH:12][C:11]([CH3:18])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.O1CCCC1.[OH-].[Na+]>O>[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([CH3:18])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58158937methyl 1-(3,5-dichloropyridin-2-yl)-3-methyl-1H-pyrazole-5-carboxylate

Product 1

HCID 581589311-(3,5-dichloropyridin-2-yl)-3-methyl-1H-pyrazole-5-carboxylic acidYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a 100 mL flask, methyl 1-(3,5-dichloropyridin-2-yl)-3-methyl-1H-pyrazole-5-carboxylate (1.00 g, 3.49 mmol), tetrahydrofuran (10 mL), water (10 mL) and sodium hydroxide (0.14 g, 3.49 mmol) were added sequentially. After being stirred for 40 minutes at room temperature, all of the starting materials had disappeared. Then water (50 mL) was added. The mixture was extracted with ethyl acetate (30 mL) and the aqueous layer was acidified with concentrated hydrochloric acid to pH of 2˜3, and extracted with ethyl acetate (3×80 mL), the organic layer was washed with saturated brine (100 mL), dried over anhydrous magnesium sulfate and concentrated by rotary evaporator to give the product (0.91 g) as a white solid in 96% yield. Melting point: 227-228° C.

Workup

  1. extractionThe mixture was extracted with ethyl acetate (30 mL)
  2. extractionextracted with ethyl acetate (3×80 mL)
  3. washthe organic layer was washed with saturated brine (100 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-4d5c882361fe46a2846b81f403dbab55
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Reaction notes

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