Chloroacetaldehyde → 7-Ethylimidazo[1,2-a]pyridine

HRID 1095738Notes

Reaction equation

HRID 1095738 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]=[C:5]([NH2:9])[CH:4]=1)[CH3:2].Cl[CH2:11][CH:12]=O>CCO>[CH2:1]([C:3]1[CH:8]=[CH:7][N:6]2[CH:11]=[CH:12][N:9]=[C:5]2[CH:4]=1)[CH3:2]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 1184254-Ethylpyridin-2-amine

Product 1

HCID 181844637-Ethylimidazo[1,2-a]pyridineYield 98.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 4-ethylpyridin-2-amine (3.21 g, 8.19 mmol), and chloroacetaldehyde (50% aqueous solution, 2.6 ml, 10.5 mmol) in EtOH (10 ml) was refluxed vigorously for 12 hours. The reaction mixture was concentrated, and the residue was suspended in saturated aqueous sodium bicarbonate solution. The aqueous mixture was extracted with CH2Cl2 and EtOAc, and the combined organic extracts were dried over Na2SO4, filtered and concentrated to afford the desired product (1.18 g, 98% yield) as a viscous oil. MS APCI (+) m/z 147.2 (M+1) detected.

Workup

  1. temperaturewas refluxed vigorously for 12 hours
  2. concentrationThe reaction mixture was concentrated
  3. extractionThe aqueous mixture was extracted with CH2Cl2 and EtOAc
  4. dry with materialthe combined organic extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a14ef65495744592aceb2fbe75dcfb13
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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