Sulfuric Acid → 4-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamide

HRID 262285Notes

Reaction equation

HRID 262285 reaction equation
[Cl:1][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][CH3:14])[N:11]=[CH:12][C:3]=12.S(=O)(=O)(O)[OH:16]>>[Cl:1][C:2]1[C:7]([C:8]([NH2:9])=[O:16])=[CH:6][N:5]=[C:4]2[N:10]([CH2:13][CH3:14])[N:11]=[CH:12][C:3]=12

Participants

3

Reactant 2

HCID 1118Sulfuric AcidHCID 213205064-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitrile

Product 1

HCID 213205094-Chloro-1-ethyl-1H-pyrazolo[3,4-b]pyridine-5-carboxamideYield 46%

Procedure

4.25 g. of 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]-pyridine-5-carbonitrile (0.02 mol.) are added to 21 ml. of concentrated sulfuric acid. The mixture is stirred at room temperature for 3 days. Then 200 ml. of ice-water are introduced, while cooling with ice-water, and the mixture is allowed to stand overnight in a refrigerator. 2.04 g. (46%) of pure 4-chloro-1-ethyl-1H-pyrazolo[3,4-b]-pyridine-5-carboxamide are obtained, m.p. 192°-193°.

Workup

  1. waitto stand overnight in a refrigerator

Sources & evidence

ORD record
ord-c1a798c2cfcc49ca9e26ff19a616be9d
Source dataset
uspto-grants-1979_05
Patent number
US04153796

Reaction notes

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