Pyridine → (3-Methoxyphenyl)hydrazine

HRID 1084828Notes

Reaction equation

HRID 1084828 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([N:8]2C3=NC=CC=C3C(C3C=CC=CC=3)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.N1C=CC=C[CH:24]=1>>[CH3:24][O:1][C:2]1[CH:3]=[C:4]([NH:8][NH2:9])[CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 1049PyridineHCID 147962521-(3-hydroxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine

Product 1

HCID 423605(3-Methoxyphenyl)hydrazine

Procedure

Therein, among the starting compounds, for example, 1-(3-hydroxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine can be obtained by heating under reflux 2-chloro-3-benzoylpyridine and 3-methoxyphenylhydrazine in pyridine to obtain the corresponding hydrazone, and subjecting to ring-closure reaction the obtained hydrazone by heating under reflux in isopentyl alcohol with the use of potassium carbonate as a deacidifying agent to obtain 1-(3-methoxyphenyl)-3-phenyl-1H-pyrazolo[3,4-b]pyridine, followed by the elimination of the methoxy group thereof with the use of a butylmercaptanaluminium chloride system.

Workup

  1. temperatureby heating under reflux 2-chloro-3-benzoylpyridine

Sources & evidence

ORD record
ord-aa31c830ac6f4fd2b5b672117b4e011e
Source dataset
uspto-grants-1991_04
Patent number
US05006520

Reaction notes

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