Chloroacetaldehyde → Imidazo[1,2-a]pyridin-5-amine

HRID 2235539Notes

Reaction equation

HRID 2235539 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([NH2:8])[N:3]=1.Cl[CH2:10][CH:11]=O>CCO>[N:1]1[CH:10]=[CH:11][N:3]2[C:4]([NH2:8])=[CH:5][CH:6]=[CH:7][C:2]=12

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 88612,6-Diaminopyridine

Product 1

HCID 327952Imidazo[1,2-a]pyridin-5-amineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

2,6-diaminopyridine (5.0 g, 46 mmol) and chloroacetaldehyde (50% wt. soln in water, 6.4 mL, 50 mmol) were dissolved in absolute EtOH (120 mL). The solution was heated at 75° C. for 1 hour. The mixture was cooled and concentrated via rotavap. The residue was taken up in saturated NaHCO3 and EtOAc. The solution was extracted with EtOAc (3 times), dried over magnesium sulfate, and concentrated to give a brown solid. 4.85 g isolated (80% yield).

Workup

  1. temperatureThe mixture was cooled
  2. concentrationconcentrated via rotavap
  3. extractionThe solution was extracted with EtOAc (3 times)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a brown solid
  7. custom4.85 g isolated (80% yield)

Sources & evidence

ORD record
ord-69ed619c89bd435f884b054d8357199a
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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