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

HRID 1523559Notes

Reaction equation

HRID 1523559 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-4de8c11f9085406d8a6bc8546e04adcd
Source dataset
uspto-grants-2015_07
Patent number
US09079890B2

Reaction notes

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