Sulfuric Acid → HCID 67485361, compound

HRID 1511031Notes

Reaction equation

HRID 1511031 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 left to stir 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 by the addition of NaOH pellets, to a pH of ˜5, at which point a solid formed. The solid was filtered and the remaining aqueous layer was extracted with EtOAc. The organic 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. waitthe slurry was left
  2. dissolutionwas fully dissolved
  3. temperatureWhile maintaining the temp below 20° C.
  4. customformed
  5. filtrationThe solid was filtered
  6. extractionthe remaining aqueous layer was extracted with EtOAc
  7. washwere washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a0acc1f3dc1446d1b34fd4e791384512
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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