4-Bromophenacyl bromide → 2-(4-Bromophenyl)-6-methylimidazo[1,2-a]pyridine

HRID 1590615Notes

Reaction equation

HRID 1590615 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][N:3]=1.[Br:9][C:10]1[CH:19]=[CH:18][C:13]([C:14](=O)[CH2:15]Br)=[CH:12][CH:11]=1>CC(C)=O>[CH3:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:15]=[C:14]([C:13]3[CH:18]=[CH:19][C:10]([Br:9])=[CH:11][CH:12]=3)[N:1]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 74544-Bromophenacyl bromideHCID 153482-Amino-5-methylpyridine

Product 1

HCID 8378932-(4-Bromophenyl)-6-methylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 18.8 g of 2-amino-5-methylpyridine and 27.8 g of p-bromophenacyl-bromide in 200 ml of acetone was refluxed for 8 hrs. The precipitate was collected and dissolved in hot methanol and 2 ml of concentrated HBr was added. The methanol solution was then basified with ammonium hydroxide. The precipitated product was collected and recrystallized from ethanol; yield 18.5 g (68%); mp 215°-216° C.

Workup

  1. temperaturewas refluxed for 8 hrs
  2. customThe precipitate was collected
  3. dissolutiondissolved in hot methanol
  4. addition2 ml of concentrated HBr was added
  5. customThe precipitated product was collected
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c91266ce09f84cb3872d2cd5c0f7720d
Source dataset
uspto-grants-1993_04
Patent number
US05204352

Reaction notes

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