Sulfuric Acid → 3-(2,6-Dimethylpyridin-3-yloxy)-5-bromopicolinamide

HRID 1511024Notes

Reaction equation

HRID 1511024 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([O:10][C:11]2[C:12]([CH3:18])=[N:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.S(=O)(=O)(O)[OH:20].[OH-].[Na+]>>[CH3:18][C:12]1[C:11]([O:10][C:4]2[C:5]([C:8]([NH2:9])=[O:20])=[N:6][CH:7]=[C:2]([Br:1])[CH:3]=2)=[CH:16][CH:15]=[C:14]([CH3:17])[N:13]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 674864525-Bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile

Product 1

HCID 679943583-(2,6-Dimethylpyridin-3-yloxy)-5-bromopicolinamideYield 92%

Procedure

To 5-bromo-3-(2,6-dimethylpyridin-3-yloxy)picolinonitrile (25 g, 82 mmol) was added concentrated sulfuric acid (25 ml) and the mixture stirred at ambient temperature over night. The mixture was poured onto ice (500 ml) and the aqueous mixture neutralized using 50% NaOH. A solid formed at pH 7. The solid was collected and dried in vacuo to afford 3-(2,6-dimethylpyridin-3-yloxy)-5-bromopicolinamide (24.2 g, 92%).

Workup

  1. additionThe mixture was poured onto ice (500 ml)
  2. customA solid formed at pH 7
  3. customThe solid was collected
  4. customdried in vacuo

Sources & evidence

ORD record
ord-02ba6816471e471f9eda5177d05a3060
Source dataset
uspto-grants-2012_07
Patent number
US08212045B2

Reaction notes

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