2-Aminopyridine → HCID 70518469, compound

HRID 1649010Notes

Reaction equation

HRID 1649010 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:13](=O)[CH:14]([Br:16])[CH3:15])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][N:20]=1>C(#N)C>[OH2:12].[BrH:16].[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[N:18]=[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]3[C:14]=2[CH3:15])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[Cl:1][C:2]1[CH:3]=[C:4]([C:13]2[N:18]=[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][N:20]3[C:14]=2[CH3:15])[CH:5]=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.[BrH:16]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 130510666-(2-Bromo-1-oxopropyl)-8-chloro-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 70518469HCID 70518469, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

8-Chloro-6-(α-bromopropionyl)-3,4-dihydrocarbostyril (4 g), 2-aminopyridine (3.57 g) and acetonitrile (20 ml) were refluxed for 3 hours. The reaction mixture was concentrated to dryness and the residue (oily product) was washed with water. Then, the residue was dissolved in acetone and 48% hydrobromic acid was added to the solution to adjust pH to about 1 and crystals which formed were crystallized by filtration. The crude crystals thus obtained were recrystallized from water to give 2.74 g of 8-chloro-6-(3-methylimidazo[1,2-a]-pyridine-2-yl)-3,4-dihydrocarbostyril monohydrobromide hemihydrate.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. washthe residue (oily product) was washed with water
  3. dissolutionThen, the residue was dissolved in acetone
  4. addition48% hydrobromic acid was added to the solution
  5. customformed
  6. customwere crystallized by filtration
  7. customThe crude crystals thus obtained
  8. customwere recrystallized from water

Sources & evidence

ORD record
ord-65933ba5b218442aabed7e8977ee5cf3
Source dataset
uspto-grants-1983_11
Patent number
US04414390

Reaction notes

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