(4-Chlorophenyl)hydrazine → 3H-Pyrazolo[4,3-c]pyridin-3-one

HRID 1194530Notes

Reaction equation

HRID 1194530 reaction equation
ClC1C=CC([NH:8][NH2:9])=CC=1.Cl[C:11]1[C:16]([C:17]([O:19]CC)=O)=[CH:15][N:14]=[C:13]2CCC[C:12]=12>C(O)CCC>[N:8]1[C:11]2=[CH:12][CH:13]=[N:14][CH:15]=[C:16]2[C:17](=[O:19])[N:9]=1

Participants

4

Reactant 2

HCID 70624(4-Chlorophenyl)hydrazineHCID 13713228HCID 13713228, compound

Product 1

HCID 183298913H-Pyrazolo[4,3-c]pyridin-3-one

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1.1 g of p-chlorophenylhydrazine and 1.9 of ethyl 4-chloro-6,7-dihydro-5H-cyclopenta[b]-pyridine-3-carboxylate (Example 2a) in 100 mL of n-butanol is refluxed for 24 hours under nitrogen atmosphere. The precipitate is collected and recrystallized from ethanol to yield 2-p-chlorophenyl-2,3,5,6,7,8-hexahydrocyclopentab]pyrazolo[3,4-d]pyridin-3-one, m.p. above 350°, showing IR peaks at 900, 835, 805, 798, 765, and 740 cm-1.

Workup

  1. temperatureis refluxed for 24 hours under nitrogen atmosphere
  2. customThe precipitate is collected
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-c2b33ff3a78c46bf833a8b09fe37b790
Source dataset
uspto-grants-1989_03
Patent number
US04814450

Reaction notes

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