(4-Chlorophenyl)hydrazine → HCID 178515178, compound

HRID 649574Notes

Reaction equation

HRID 649574 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH2:9])=[CH:4][CH:3]=1.Cl[C:11]1[C:16]([C:17](OCC)=[O:18])=[CH:15][N:14]=[C:13]2[CH2:22][CH2:23][CH2:24][C:12]=12>C(O)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:17](=[O:18])[C:16]3[C:11]([C:12]4[CH2:24][CH2:23][CH2:22][C:13]=4[NH:14][CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

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

Product 1

HCID 178515178HCID 178515178, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1.1 g of p-chlorophenylhydrazine and 1.9 g 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-hexahydrocyclopenta[b]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-b5197ec791444dc6b3b706707361dfa3
Source dataset
uspto-grants-1988_04
Patent number
US04740512

Reaction notes

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