Chloroacetaldehyde → Imidazo[1,2-a]pyridine-8-carbonitrile

HRID 524090Notes

Reaction equation

HRID 524090 reaction equation
[NH2:1][C:2]1[N:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].Cl[CH2:11][CH:12]=O>CCO>[N:1]1[CH:11]=[CH:12][N:9]2[CH:8]=[CH:7][CH:6]=[C:3]([C:4]#[N:5])[C:2]=12

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 8182592-Amino-3-cyanopyridine

Product 1

HCID 15098893Imidazo[1,2-a]pyridine-8-carbonitrileYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 2-aminonicotinonitrile (1.0 g, 8.39 mmol) in EtOH (10 ml) in a 20 ml sealed vial was added 2-chloroacetaldehyde (1.611 ml, 9.23 mmol) vial was then sealed and heated to 120° C. overnight. Reaction was cooled to RT and quenched with 2N Na2CO3, removed EtOH in vaccuo and extracted with DCM×3. Combined organics and washed with water then brine×2. Dired over sodium sulfate and removed solvent to give title compound as a yellow brown solid (1.2 g, 8.38 mmol, 100% yield) was verified by MS (ES+) C8H5N3 requires: 143 found: 144 [M+H]+

Workup

  1. customwas then sealed
  2. customReaction
  3. temperaturewas cooled to RT
  4. customquenched with 2N Na2CO3
  5. customremoved EtOH in vaccuo
  6. extractionextracted with DCM×3
  7. washCombined organics and washed with water
  8. customDired over sodium sulfate and removed solvent

Sources & evidence

ORD record
ord-a21a5fc9c2ce4cb7965b7bd4b5b72760
Source dataset
uspto-grants-2016_05
Patent number
US09340514B2

Reaction notes

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