HCID 2799775, compound → Imidazo[1,5-a]pyridine-3-acetonitrile

HRID 2199048Notes

Reaction equation

HRID 2199048 reaction equation
[C:1]([CH2:3][C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=O)#[N:2]>P(Cl)(Cl)(Cl)=O>[C:1]([CH2:3][C:4]1[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]2=[CH:7][N:6]=1)#[N:2]

Participants

3

Reactant 1

HCID 2799775HCID 2799775, compound

Product 1

HCID 21265783Imidazo[1,5-a]pyridine-3-acetonitrile

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

Heat under reflux for 0.5 hours a mixture of 9 gm (0.06 mol) 2-cyano-N-(2-pyridylmethyl)acetamide and 100 ml phosphorous oxychloride. Cool the reaction mixture to room temperature and remove the phosphorus oxychloride under reduced pressure. Partition the residue between chloroform and a solution of sodium bicarbonate. Separate the chloroform layer and dry over anhydrous potassium carbonate. Filter and remove the chloroform under reduced pressure. Chromatograph the resulting residue on silica gel using ethyl acetate-chloroform to give the desired product, 3-cyanomethyl imidazo[1,5-a]pyridine, as determined by IR, NMR and elemental analysis, m.p. 64°-66°.

Workup

  1. temperatureHeat
  2. temperatureunder reflux for 0.5 hours
  3. customremove the phosphorus oxychloride under reduced pressure
  4. customPartition the residue between chloroform
  5. customSeparate the chloroform layer
  6. dry with materialdry over anhydrous potassium carbonate
  7. filtrationFilter
  8. customremove the chloroform under reduced pressure

Sources & evidence

ORD record
ord-416af44747254a58ba5d0a71748e93d0
Source dataset
uspto-grants-1982_11
Patent number
US04361567

Reaction notes

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