2-Aminopyridine → 2-Butylimidazo(1,2-a)pyridine

HRID 37210Notes

Reaction equation

HRID 37210 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.Br[CH2:9][C:10](=O)[CH2:11][CH2:12][CH2:13][CH3:14]>CC(C)=O>[CH2:11]([C:10]1[N:1]=[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]2[CH:9]=1)[CH2:12][CH2:13][CH3:14]

Participants

4

Reactant 2

HCID 104392-AminopyridineHCID 124317331-Bromohexan-2-one

Product 1

HCID 151299072-Butylimidazo(1,2-a)pyridineYield 53.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

A mixture of 6 g of 2-amino pyridine and 60 ml of anhydrous acetone was added to a mixture of 16 g of the product of Stage B and 20 ml of acetone at ambient temperature. The mixture was refluxed for one hour and the acetone was partially distilled. The mixture was allowed to return to ambient temperature, ice-cooled, separated and washed with ethyl ether. The insoluble part was dissolved in a saturated solution of sodium carbonate and extraction was carried out with ethyl acetate. The extracts were washed with water saturated in sodium chloride, dried and filtered to obtain 5.9 g of the expected product in the form of a yellow oil.

Workup

  1. temperatureThe mixture was refluxed for one hour
  2. distillationthe acetone was partially distilled
  3. customto return to ambient temperature
  4. temperatureice-cooled
  5. customseparated
  6. washwashed with ethyl ether
  7. dissolutionThe insoluble part was dissolved in a saturated solution of sodium carbonate and extraction
  8. washThe extracts were washed with water saturated in sodium chloride
  9. customdried
  10. filtrationfiltered

Sources & evidence

ORD record
ord-0a296b96e6cb4a569488c76c832ec44c
Source dataset
uspto-grants-1995_05
Patent number
US05420138

Reaction notes

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