Sulfuric Acid → HCID 67485361, compound

HRID 1809594Notes

Reaction equation

HRID 1809594 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.S(=O)(=O)(O)[OH:19].[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:19])=[N:6][CH:7]=1

Participants

5

Reactant 3

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

Product 1

HCID 67485361HCID 67485361, compoundYield 98.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A flask was charged with 5-bromo-3-(2-methylpyridin-3-yloxy)picolinonitrile (60 g, 207 mmol) and sulfuric acid (203 g, 2068 mmol). The reaction was stirred at ambient temperature overnight. Water (500 mL) was added carefully and neutralized using 50% sodium hydroxide to pH 5.0. The mixture was extracted with dichloromethane and ethyl acetate, dried and concentrated to afford 5-bromo-3-(2-methylpyridin-3-yloxy)picolinamide (63.0 g, 204 mmol, 98.9% yield) as yellow solid.

Workup

  1. extractionThe mixture was extracted with dichloromethane and ethyl acetate
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a01800f6a1d5483bb90a926ab331c753
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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