Sulfuric Acid → HCID 67485361, compound

HRID 534029Notes

Reaction equation

HRID 534029 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:17])=[N:13][CH:14]=[CH:15][CH:16]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[OH:18]S(O)(=O)=O.[OH-].[Na+]>O>[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:17])=[N:13][CH:14]=[CH:15][CH:16]=2)[C:5]([C:8]([NH2:9])=[O:18])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 67485726HCID 67485726, compound

Product 1

HCID 67485361HCID 67485361, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 5-bromo-3-(2-methylpyridin-3-yloxy)picolinonitrile (15 g, 52 mmol) was added concentrated H2SO4 (30 mL) and the slurry was stirred overnight, at which point the material was fully dissolved. The reaction was poured into 0° C. water in small portions. While maintaining the temp below 20° C., the aqueous layer was basified to about a pH of 5 by the addition of NaOH pellet, at which point a solid formed. The solid was filtered, and the remaining aqueous layer was extracted with EtOAc. The organics layers, combined with the solid, were washed with brine, dried over MgSO4 and concentrated in vacuo to yield 5-bromo-3-(2-methylpyridin-3-yloxy)picolinamide (11 g, 69%).

Workup

  1. dissolutionwas fully dissolved
  2. temperatureWhile maintaining the temp below 20° C.
  3. customformed
  4. filtrationThe solid was filtered
  5. extractionthe remaining aqueous layer was extracted with EtOAc
  6. washwere washed with brine
  7. dry with materialdried over MgSO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62fa070177814d6bb31ca29c22a33a3f
Source dataset
uspto-grants-2014_10
Patent number
US08853409B2

Reaction notes

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