2-Amino-3-methylpyridine → HCID 4062357, compound

HRID 2238639Notes

Reaction equation

HRID 2238639 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1.Cl[CH2:10][C:11]([CH2:13][C:14](=O)[CH3:15])=[O:12]>O1CCCC1.C(OCC)C.C(OCC)(=O)C>[CH3:15][C:14]1[N:1]=[C:2]2[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]2[C:13]=1[C:11](=[O:12])[CH3:10]

Participants

6

Reactant 2

HCID 153472-Amino-3-methylpyridineHCID 144968561-Chloro-2,4-pentanedione

Product 1

HCID 4062357HCID 4062357, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2 g of 2-amino-3-picoline was dissolved in a mixture solvent of 10 mL of tetrahydrofuran and 5 mL of diethyl ether, 4.4 mL of 3-chloroacetyl acetone was added, and heated overnight under reflux. The reaction mixture was cooled back to room temperature, diluted with ethyl acetate, and then washed with water and with saturated brine in the subsequent order. After drying the organic layer over anhydrous magnesium sulfate, the insolubles were filtered, and the filtrate was concentrated under reduced pressure. The obtained residue was dissolved in a small amount of chloroform and solidified by adding hexane, to obtain 664 mg of 1-(2,8-dimethylimidazo[1,2-a]pyridin-3-yl)ethanone [38-1] as a light grey solid.

Workup

  1. additionwas added
  2. temperatureheated overnight
  3. temperatureunder reflux
  4. washwashed with water and with saturated brine in the subsequent order
  5. dry with materialAfter drying the organic layer over anhydrous magnesium sulfate
  6. filtrationthe insolubles were filtered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. dissolutionThe obtained residue was dissolved in a small amount of chloroform
  9. additionby adding hexane

Sources & evidence

ORD record
ord-9f7a89efaebc4babb10979bb7299ae73
Source dataset
uspto-grants-2010_05
Patent number
US07718801B2

Reaction notes

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