Ammonia → Imidazo[1,5-a]pyridine-3-acetonitrile

HRID 566253Notes

Reaction equation

HRID 566253 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.N>C(Cl)(Cl)Cl>[CH:7]1[N:6]=[C:4]([CH2:3][C:1]#[N:2])[N:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=12

Participants

5

Reactant 3

HCID 222AmmoniaHCID 24813Phosphorus oxychlorideHCID 2799775HCID 2799775, compound

Product 1

HCID 21265783Imidazo[1,5-a]pyridine-3-acetonitrileYield 35.9%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Cyano-N-(2-pyridylmethyl)acetamide (15.51 g) was dissolved in chloroform (80 ml). To the solution was added phosphorus oxychloride (40 ml), which was refluxed for 4 hours. The reaction mixture was added to ice-water in limited amounts, to which was added a 25% aqueous ammonia (140 ml) to neutralize, which was then shaken. The aqueous layer was subjected to extraction with ethyl acetate (150 ml) twice. The organic layers were combined and dried over anhydrous magnesium sulfate, followed by concentration. The concentrate was purified by means of a column chromatography (carrier: silica gel, 250 g, developing solvent: ethyl acetate) to afford the title compound (5.00 g).

Workup

  1. temperaturewas refluxed for 4 hours
  2. extractionThe aqueous layer was subjected to extraction with ethyl acetate (150 ml) twice
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationfollowed by concentration
  5. customThe concentrate was purified by means of a column chromatography (carrier: silica gel, 250 g, developing solvent: ethyl acetate)

Sources & evidence

ORD record
ord-721a2bd50ebb4bc3a5edf42059a93a46
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Reaction notes

Loading…