Methyl Isocyanate → 2-Phenylpyrazolo[1,5-a]pyridine-3-carbonitrile

HRID 1650748Notes

Reaction equation

HRID 1650748 reaction equation
CN=C=O.[C:5]1([C:11]2[C:19]([CH:20]=[N:21]O)=[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]3[N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(Cl)Cl.C(Cl)(Cl)Cl>[C:5]1([C:11]2[C:19]([C:20]#[N:21])=[C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][N:13]3[N:12]=2)[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 54361733HCID 54361733, compound

Product 1

HCID 137381542-Phenylpyrazolo[1,5-a]pyridine-3-carbonitrileYield 43.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of methyl isocyanate (0.19 g) in methylene chloride (2 ml) was added dropwise to a mixture of 2-phenylpyrazolo[1,5-a]pyridine-3-carbaldehyde oxime (0.52 g) in chloroform (4 ml) with stirring and ice-cooling. The mixture was stirred at room temperature for 2 hours and allowed to stand at room temperature overnight. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel (20 g) with methylene chloride as an eluent The fractions containing the object compound were combined (20 ml) and evaporated in vacuo. The residue was recrystallized from ethyl acetate to give 2-phenylpyrazolo[1,5-a]pyridine-3-carbonitrile (0.21 g).

Workup

  1. temperatureice-cooling
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. customThe solvent was evaporated in vacuo
  4. customthe residue was chromatographed on silica gel (20 g) with methylene chloride as an eluent The fractions
  5. additioncontaining the object compound
  6. customevaporated in vacuo
  7. customThe residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-20f18a6b6d354dfa9e6e9a5ccad99fa2
Source dataset
uspto-grants-1990_05
Patent number
US04925849

Reaction notes

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