Methanol → 1-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carboxylic acid

HRID 453079Notes

Reaction equation

HRID 453079 reaction equation
[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([O:16]CC)=[O:15])=[CH:12][C:11]([O:19][CH2:20][C:21]#[CH:22])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.CO.O.[OH-].[Na+]>CCOCC>[Cl:1][C:2]1[C:3]([N:9]2[C:13]([C:14]([OH:16])=[O:15])=[CH:12][C:11]([O:19][CH2:20][C:21]#[CH:22])=[N:10]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962Water3×HCID 14798Sodium HydroxideHCID 58158934ethyl 1-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carboxylate

Product 1

HCID 581589381-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carboxylic acidYield 98.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a 100 mL flask, ethyl 1-(3,5-dichloropyridin-2-yl)-3-(prop-2-ynyloxy)-1H-pyrazole-5-carboxylate (0.3 g, 0.88 mmol), methanol (10 mL), water (10 mL) and sodium hydroxide (0.04 g, 0.88 mmol) were added. The reaction mixture was stirred at room temperature for 1 hour. When reacted completely, water (40 mL) was added. The water (40 mL), ether (50 mL) were added and partitioned, acidified with concentrated hydrochloric acid to pH of 4, extracted with ethyl acetate (150 mL). The organic layer was washed with saturated brine (50 mL), dried over anhydrous magnesium sulfate and concentrated at reduced pressure to give the product (0.27 g) as slight yellow solid in 73% yield. Melting point: 151-157° C.

Workup

  1. customWhen reacted completely
  2. custompartitioned
  3. extractionextracted with ethyl acetate (150 mL)
  4. washThe organic layer was washed with saturated brine (50 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-19813de731ae4613be2e643d35dc2c21
Source dataset
uspto-grants-2013_07
Patent number
US08492409B2

Reaction notes

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