Hydrazine hydrate (1:1) → HCID 178507410, compound

HRID 255896Notes

Reaction equation

HRID 255896 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)=[CH:6][CH:5]=1)([O-])=O.O.NN>[Ni].CO>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:14]=[CH:13][NH:12][N:11]=2)=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178526520HCID 178526520, compound

Product 1

HCID 178507410HCID 178507410, compoundYield 95.7%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent2×

Procedure

To a refluxing suspension of 3-(4-nitrophenyl)-pyrazole (18 g) and Raney nickel (3.3 g) in methanol (190 ml) was added dropwise a solution of 85% hydrazine hydrate (22 g) in methanol (50 ml). The solution was refluxed for 30 minutes more, filtered and evaporated to dryness. The oily residue, after crystallization from water, furnished 14.5 g of 3-(4-aminophenyl)-pyrazole; M.p. 104° C. 3-(3-Aminophenyl)-pyrazole, M.p. 144°-145° C., was prepared in a similar manner starting from 3-nitroacetophenone.

Workup

  1. temperatureThe solution was refluxed for 30 minutes more
  2. filtrationfiltered
  3. customevaporated to dryness
  4. customThe oily residue, after crystallization from water

Sources & evidence

ORD record
ord-aef1a6371baa43cba0ac3450d52e280c
Source dataset
uspto-grants-1987_10
Patent number
US04699915

Reaction notes

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