Sulfuric Acid → 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide

HRID 534110Notes

Reaction equation

HRID 534110 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=2[CH3:16])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH:19]S(O)(=O)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][N:14]([CH3:17])[C:15]=2[CH3:16])[C:5]([C:8]([NH2:9])=[O:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 674868715-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile

Product 1

HCID 674864005-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamideYield 100%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinonitrile (7.0 g, 23 mmol) and H2SO4 (56 g, 570 mmol) and the reaction was stirred at ambient temperature overnight. The reaction was cooled in an ice bath and water (100 mL) was carefully added 40% NaOH solution was slowly added till the pH was about 12. The mixture was extracted with ethyl acetate and dichloromethane, and the combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo to afford 5-bromo-3-(1,3,5-trimethyl-1H-pyrazol-4-yloxy)picolinamide (7.4 g, 23 mmol, 100% yield) as light yellow solid.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. additionwas slowly added till the pH was about 12
  3. extractionThe mixture was extracted with ethyl acetate and dichloromethane
  4. dry with materialthe combined organic layers were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-89911f57b6e24a83bce73c85057f7e63
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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