Sodium Hydroxide → 2-Amino-3-bromo-6-methylpyridine

HRID 2294887Notes

Reaction equation

HRID 2294887 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][CH:3]=1.[Br:9]Br.[OH-].[Na+]>S(=O)(=O)(O)O.O>[NH2:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[Br:9]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 157652-Amino-6-methylpyridineHCID 24408Bromine

Product 1

HCID 27344162-Amino-3-bromo-6-methylpyridineYield 55.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

32.4 g (0.3 mole) of 6-aminopicoline was dissolved in a mixture of 28 g of conc. sulfuric acid and 120 ml of water and the resulting solution was cooled in ice water. 52.8 g (0.33 mole) of bromine was added dropwise to the solution over 30 minutes at 0° C. The reaction solution was stirred for 20 minutes at room temperature and neutralized with cold aqueous NaOH solution. The resultant was filtered and the solid was purified with column chromatography using methylene chloride and ethyl acetate as an eluent to obtain 31 g of the title compound (yield 55%).

Workup

  1. filtrationThe resultant was filtered
  2. customthe solid was purified with column chromatography

Sources & evidence

ORD record
ord-3937fc1e153a4492b650464d69a4578b
Source dataset
uspto-grants-1997_11
Patent number
US05691348

Reaction notes

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