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

HRID 53522Notes

Reaction equation

HRID 53522 reaction equation
C([O-])(=O)C.[Na+].[NH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH3:14])=[N:11][CH:12]=1.[Br:15]Br.[OH-].[Na+]>C(O)(=O)C.O>[NH2:6][C:7]1[C:12]([Br:15])=[N:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1

Participants

7

Reactant 4

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

Product 1

HCID 152093242-Bromo-6-methoxypyridin-3-amineYield 70.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Sodium acetate (1.6 g) was added to a solution of 5-amino-2-methoxypyridine (2.5 g) in acetic acid (15 ml). To the resulting solution bromine (3.0 g) was added dropwise, and the mixture was stirred for 20 min., and then added to a solution of sodium hydroxide (10 g) in water (100 ml). The product was extracted with ethyl acetate (50 ml), dried (anhydrous magnesium sulfate), and concentrated in vacuo. The product was purified over a silica gel column (ethyl acetate/hexane, 1:4) to give 2.7 g of the title compound, suitable for use in the next reaction.

Workup

  1. extractionThe product was extracted with ethyl acetate (50 ml)
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. concentrationconcentrated in vacuo
  4. customThe product was purified over a silica gel column (ethyl acetate/hexane, 1:4)

Sources & evidence

ORD record
ord-9500bda899ae40a8a0a8cc6f4800f5ca
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Reaction notes

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