Benzene → 5-(o-Aminophenyl)-4-nitropyrazole

HRID 1659325Notes

Reaction equation

HRID 1659325 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].C1C=CC=CC=1.O.[NH2:22][NH2:23]>O>[NH2:5][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=1[C:2]1[NH:23][N:22]=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 241BenzeneHCID 24654Hydrazine hydrate (1:1)2×HCID 112758084-Chloro-3-nitroquinoline

Product 1

HCID 205602605-(o-Aminophenyl)-4-nitropyrazoleYield 83%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 20.8 g (0.1 mole) of 4-chloro-3-nitroquinoline, 40 ml of benzene and 40 ml of hydrazine hydrate is refluxed for 2 hours, then cooled. The separated phase containing hydrazine hydrate is diluted with 150 ml of water. Yellow-white crystals separate. Thus, 16.8 g (83%) of 5-(o-aminophenyl)-4-nitropyrazole are obtained. M.p.: 175°-176° C. (ethanol).

Workup

  1. temperatureis refluxed for 2 hours
  2. temperaturecooled
  3. customYellow-white crystals separate

Sources & evidence

ORD record
ord-599f851ef7c24e7fa1bd7049325a8a63
Source dataset
uspto-grants-1981_12
Patent number
US04303660

Reaction notes

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