Sodium Hydroxide → 2-Bromo-6-methoxy-4-methylpyridin-3-amine

HRID 53530

Reaction equation

HRID 53530 reaction equation
[Br:1]Br.[NH2:3][C:4]1[C:5]([CH3:12])=[CH:6][C:7]([O:10][CH3:11])=[N:8][CH:9]=1.[OH-].[Na+]>C(O)(=O)C.C([O-])(=O)C.[Na+].O>[NH2:3][C:4]1[C:9]([Br:1])=[N:8][C:7]([O:10][CH3:11])=[CH:6][C:5]=1[CH3:12]

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 24408BromineHCID 2431706-Methoxy-4-methylpyridin-3-amine

Product 1

HCID 199600552-Bromo-6-methoxy-4-methylpyridin-3-amineYield 73.4%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 517045Sodium AcetateSolvent

Procedure

Bromine (4.8 g) was added in one portion to a mixture of 5-amino-2-methoxy-4-methylpyridine (3.9 g) in acetic acid (25 ml) and sodium acetate (4.0 g). The resulting mixture was stirred for 20 min. and then added to a solution of sodium hydroxide (15 g) in water (200 ml). The product was extracted with chloroform, dried (anhydrous magnesium sulfate), concentrated, and purified on a silica gel column (methylene chloride/ethyl acetate, 19:1→4:1) to give 4.5 g of the title compound, suitable for use in the next reaction.

Workup

  1. extractionThe product was extracted with chloroform
  2. dry with materialdried (anhydrous magnesium sulfate)
  3. concentrationconcentrated
  4. custompurified on a silica gel column (methylene chloride/ethyl acetate, 19:1→4:1)

Sources & evidence

ORD record
ord-799afdfeca8e49de85cda50d03081884
Source dataset
uspto-grants-1997_04
Patent number
US05620974

Linked notes

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