Hydrazine hydrate (1:1) → HCID 178507574, compound

HRID 1708851Notes

Reaction equation

HRID 1708851 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]([C:16]2[CH:20]=[CH:19][NH:18][N:17]=2)[C:12]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-])=O)[CH:24]=2)=[N:11]1.O.NN>[Ni].CO>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:10]1[C:14](=[O:15])[CH:13]([C:16]2[CH:20]=[CH:19][NH:18][N:17]=2)[C:12]([NH:21][C:22](=[O:32])[C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([NH2:29])[CH:24]=2)=[N:11]1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178522630HCID 178522630, compound

Product 1

HCID 178507574HCID 178507574, compoundYield 68.6%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

Next, 197.5 g (0.4 mol) of the 1-(2,4,6-trichlorophenyl)-3-(3-nitrobenzamido)-4-pyrazolyl-5-oxo-2-pyrazoline was added to 2l of methanol, to which was added a small amount of Raney nickel. Then 120 ml of hydrazine hydrate was slowly added dropwise with heating and stirring, the mixture rcacted for about 1.5 hours, after which the insolubles were filtered out (while the mixture was hot). The filtrate was poured into water, and the deposited crystals were then filtered and washed with methanol to obtain 127.2 g (68%) of 1-(2,4,6-trichlorophenyl)-3-(3-aminobenzamido)-4-pyrazolyl-5-oxo-2-pyrazoline.

Workup

  1. temperaturewith heating
  2. filtrationafter which the insolubles were filtered out (while the mixture
  3. additionThe filtrate was poured into water
  4. filtrationthe deposited crystals were then filtered
  5. washwashed with methanol

Sources & evidence

ORD record
ord-95f66f2743ba42c6a1fb16ba67dd9700
Source dataset
uspto-grants-1990_08
Patent number
US04946771

Reaction notes

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