Hydroxyamine hydrochloride → 7-(3-Pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 1278203Notes

Reaction equation

HRID 1278203 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[N:13]=[CH:14][C:15]([CH:16]=O)=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1.Cl.[NH2:19]O>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]#[N:19])=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 443297Hydroxyamine hydrochlorideHCID 21163078HCID 21163078, compound

Product 1

HCID 112183037-(3-Pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.01 mole of 7-(3-pyridyl)pyrazolo-[1,5-a]pyrimidine-3-carboxaldehyde and 0.011 mole of hydroxylamine hydrochloride in 25 ml. of ethanol is heated on a steam bath for 3 hours. The solvent is removed and to the residue is added 25 ml. of acetic anhydride. The mixture is heated at reflux temperature for 6 hours and the solvent is removed in vacuo. The residue is partitioned between dichloromethane and sodium bicarbonate solution and the organic layer is separated, dried over magnesium sulfate, and the solvent removed to give the product of the example, m.p. 258°-260° C.

Workup

  1. customThe solvent is removed and to the residue
  2. additionis added 25 ml
  3. temperatureThe mixture is heated
  4. temperatureat reflux temperature for 6 hours
  5. customthe solvent is removed in vacuo
  6. customThe residue is partitioned between dichloromethane and sodium bicarbonate solution
  7. customthe organic layer is separated
  8. dry with materialdried over magnesium sulfate
  9. customthe solvent removed
  10. customto give the product of the example, m.p. 258°-260° C.

Sources & evidence

ORD record
ord-6f5245655a8544df90f812649e2d2e9b
Source dataset
uspto-grants-1981_07
Patent number
US04281000

Reaction notes

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