2-Aminopyridine → HCID 13051053, compound

HRID 1649009Notes

Reaction equation

HRID 1649009 reaction equation
[Br:1][CH:2]([CH3:17])[C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10](=[O:16])[CH2:9][CH2:8]2)=O.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>C(#N)C>[BrH:1].[CH3:17][C:2]1[N:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]2=[N:18][C:3]=1[C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10](=[O:16])[CH2:9][CH2:8]2

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 13051051HCID 13051051, compound

Product 1

HCID 13051053HCID 13051053, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-(α-Bromopropionyl)-1-methyl-3,4-dihydrocarbostyril (5 g), 2-aminopyridine (4.77 g) and acetonitrile (20 ml) were refluxed for 1.5 hours. The reaction mixture was cooled with ice water and crystals which precipitated were collected by filtration. The crystals were dissolved in acetone and the solution was adjusted to pH of about 1 by the addition of 48% hydrobromic acid. Crystals which formed were collected by filtration and recrystallized from water to give 5.68 g of 6-(3-methylimidazo[1,2-a]pyridine-2-yl)-1-methyl-3,4-dihydrocarbostyril monohydrobromide.

Workup

  1. customprecipitated
  2. filtrationwere collected by filtration
  3. dissolutionThe crystals were dissolved in acetone
  4. additionthe solution was adjusted to pH of about 1 by the addition of 48% hydrobromic acid
  5. customCrystals which formed
  6. filtrationwere collected by filtration
  7. customrecrystallized from water

Sources & evidence

ORD record
ord-51c080bf78404c0b8672efafe70479ec
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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