Hydrogen Bromide → 2-Amino-3-chloro-5-pyridyl bromomethyl ketone

HRID 981327Notes

Reaction equation

HRID 981327 reaction equation
[Br:1]Br.[NH2:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([C:11](=[O:13])[CH3:12])=[CH:6][N:5]=1.Br>C(O)(=O)C>[Br:1][CH2:12][C:11]([C:7]1[CH:8]=[C:9]([Cl:10])[C:4]([NH2:3])=[N:5][CH:6]=1)=[O:13]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 24408BromineHCID 143713831-(6-Amino-5-chloropyridin-3-YL)ethan-1-one

Product 1

HCID 143713842-Amino-3-chloro-5-pyridyl bromomethyl ketoneYield 74.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

16 g (0.1 mol) of bromine are added dropwise to a solution of 17.05 g (0.1 mol) of 2-amino-3-chloro-5-acetylpyridine in a mixture of 19.3 g of hydrogen bromide (47% strength aqueous solution; 0.11 mol) and 500 ml of glacial acetic acid. The mixture is subsequently stirred for two hours, brought to pH 8 and extracted with ethyl acetate. Drying and evaporation gives 18.5 g (74%) of the title compound, melting point 134° C.

Workup

  1. extractionextracted with ethyl acetate
  2. customDrying
  3. customevaporation

Sources & evidence

ORD record
ord-b1db0434e8f24d75838f3236981d4cad
Source dataset
uspto-grants-1991_02
Patent number
US04990620

Reaction notes

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