Phenacyl bromide → 2-phenylimidazo[1,2-a]pyridine

HRID 904608Notes

Reaction equation

HRID 904608 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O>C(Cl)(Cl)Cl>[C:12]1([C:10]2[N:1]=[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][N:3]3[CH:9]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 104392-Aminopyridine

Product 1

HCID 2011362-phenylimidazo[1,2-a]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

0.1 m. Quantities of 2-aminopyridine and α-bromoacetophenone are heated in 150 ml. of chloroform at reflux for 2 hours. The chloroform is evaporated and the oily residue taken up in 10% HCl, warmed, charcoal added and filtered. The filtrate is neutralized with NH4OH and the solid product isolated and recrystallized from ethanol. The yield of product is 12.7 g., melts at 135°-137° C. and has the structure: ##STR13##

Workup

  1. customThe chloroform is evaporated
  2. temperaturewarmed
  3. additioncharcoal added
  4. filtrationfiltered
  5. customthe solid product isolated
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-75f65cedf47f4c5f8eb43f10b6550a06
Source dataset
uspto-grants-1983_12
Patent number
US04419289

Reaction notes

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