Sodium Hydroxide → 2-Bromo-6-methoxypyridin-3-amine

HRID 400575Notes

Reaction equation

HRID 400575 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][N:4]=1.C([O-])(=O)C.[Na+].[Br:15]Br.[OH-].[Na+]>C(O)(=O)C>[NH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[N:4][C:5]=1[Br:15]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24408BromineHCID 811216-Methoxy-3-pyridinylamineHCID 517045Sodium Acetate

Product 1

HCID 152093242-Bromo-6-methoxypyridin-3-amineYield 40%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A stirred mixture of 2-methoxy-5-aminopyridine (10 g, 0.081 mol, 1.0 equiv) and sodium acetate (6.6 g, 0.081 mol, 1.0 equiv) in 60 mL of acetic acid was treated dropwise with bromine (12.9 g, 0.081 mol, 1.0 equiv). After 20 minutes, the reaction mixture was poured into 1000 mL of 10% aqueous sodium hydroxide solution and extracted with three 250 mL portions of ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, and evaporated to dryness. Chromatography on SiO2 (20% hexanes in dichloromethane) gave 5-amino-6-bromo-2-methoxypyridine (6.5 g, 40% yield) as a purple solid.

Workup

  1. extractionextracted with three 250 mL portions of ethyl acetate
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. filtrationfiltered
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-299374cde1ff4f23a70bd3d2417c9210
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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