2-Amino-5-methylpyridine → 2-Amino-3-bromo-5-methylpyridine

HRID 487563Notes

Reaction equation

HRID 487563 reaction equation
[Br:1]Br.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][N:5]=1>C(Cl)Cl>[NH2:3][C:4]1[C:9]([Br:1])=[CH:8][C:7]([CH3:10])=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 153482-Amino-5-methylpyridineHCID 24408Bromine

Product 1

HCID 5193802-Amino-3-bromo-5-methylpyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Bromine (3.19 g) was added dropwise at 0° C. to a solution of 2-amino-5-picoline in 75 mL CH2Cl2. After about two hours at room temperature, the reaction was extracted with saturated sodium carbonate solution, then sodium thiosulfate solution. The combined aqueous extracts were washed with CH2Cl2, and the combined organic extracts washed with saturated NaCl, dried (Na2SO4) and concentrated giving 3.59 g crude material. The product was purified by flash chromatography on silica gel, eluting with petroleum ether with increasing amounts of CH2Cl2 (0-40%), giving 3.05 g 2-amino-3-bromo-5-picoline, m.p. 68°-70° C.

Workup

  1. extractionthe reaction was extracted with saturated sodium carbonate solution
  2. washThe combined aqueous extracts were washed with CH2Cl2
  3. washthe combined organic extracts washed with saturated NaCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customgiving 3.59 g crude material
  7. customThe product was purified by flash chromatography on silica gel
  8. washeluting with petroleum ether with increasing amounts of CH2Cl2 (0-40%)

Sources & evidence

ORD record
ord-739c1af2e33240538b0a561e1bb8c736
Source dataset
uspto-grants-1994_03
Patent number
US05296486

Reaction notes

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