Thionyl Chloride → 4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

HRID 262284Notes

Reaction equation

HRID 262284 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][CH:9]=[C:10]([C:13]([NH2:15])=O)[C:11](O)=[C:6]2[CH:5]=[N:4]1)[CH3:2].S(Cl)([Cl:18])=O>>[Cl:18][C:11]1[C:10]([C:13]#[N:15])=[CH:9][N:8]=[C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=12

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 178463021HCID 178463021, compound

Product 1

HCID 213205064-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Procedure

10.3 g. of 1-ethyl-4-hydroxy-1H-pyrazolo-[3,4-b]pyridine-5-carboxamide (0.05 mol.) and 125ml. of thionyl chloride are refluxed for 3.5 hours. After cooling, the thionyl chloride is removed in vacuo and the residue is extracted twice with 400ml. of refluxing hexane. The combined extracts are treated with charcoal, filtered and evaporated. The product, 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile, is recrystallized from a small amount of hexane, yield 2.9 g. (28%), m.p. 100°-102°.

Workup

  1. temperatureAfter cooling
  2. customthe thionyl chloride is removed in vacuo
  3. extractionthe residue is extracted twice with 400ml
  4. additionThe combined extracts are treated with charcoal
  5. filtrationfiltered
  6. customevaporated
  7. customThe product, 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile, is recrystallized from a small amount of hexane, yield 2.9 g

Sources & evidence

ORD record
ord-ee29ba74b07b45278e77c043d8a18961
Source dataset
uspto-grants-1979_05
Patent number
US04153796

Reaction notes

Loading…