Bromoacetone → 2-Methyl-8-nitroimidazo[1,2-a]pyridine

HRID 1195737Notes

Reaction equation

HRID 1195737 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:12][C:13](=O)[CH3:14]>C(O)C>[CH3:14][C:13]1[N:1]=[C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][N:3]2[CH:12]=1

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 778873-Nitropyridin-2-ylamine

Product 1

HCID 218273482-Methyl-8-nitroimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20.0 g of 2-amino-3-nitropyridine and 22 g of bromoacetone are boild in 1 l ethanol for 55 hours under reflux. The mixture is then cooled in an icebath, the crystalline hydrobromide filtered off under suction and washed with ethanol. After drying in a vacuum at 50° C. the yield of the title compound of m.p. 300° C. (decomposition) is 17.2 g.

Workup

  1. customfor 55 hours
  2. temperatureunder reflux
  3. temperatureThe mixture is then cooled in an icebath
  4. filtrationthe crystalline hydrobromide filtered off under suction
  5. washwashed with ethanol
  6. dry with materialAfter drying in a vacuum at 50° C. the yield of the title compound of m.p. 300° C. (decomposition)

Sources & evidence

ORD record
ord-b70e592395e14850af807c037bd8f1fe
Source dataset
uspto-grants-1992_05
Patent number
US05112834

Reaction notes

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