Hydrazine hydrate (1:1) → 4-[(1-Methyl-3,5-diphenyl-1H-pyrazol-4-yl)oxy]aniline

HRID 1658397Notes

Reaction equation

HRID 1658397 reaction equation
O.NN.[CH3:4][N:5]1[C:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:8]([O:16][C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[C:7]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[N:6]1>[Pd].C(O)C>[NH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][C:8]2[C:7]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[N:6][N:5]([CH3:4])[C:9]=2[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 213980591-Methyl-4-(4-nitrophenoxy)-3,5-diphenyl-1H-pyrazole

Product 1

HCID 213981014-[(1-Methyl-3,5-diphenyl-1H-pyrazol-4-yl)oxy]anilineYield 101.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Hydrazine hydrate (3 ml, 60% solution) is added to a well stirred mixture of 1-methyl-4-(p-nitrophenoxy)-3,5-diphenylpyrazole (2.56 g, 0.0069 mole), 5% Pd on carbon (0.4 g) and absolute ethanol (40 ml). Gas bubbles form immediately and an exotherm (ca. 50°C) is observed. After the reaction subsides, the reaction mixture is refluxed for 2 hours. The reaction mixture is cooled slightly and filtered to remove the catalyst. The filtrate is stripped in vacuo to give a white solid 2.4 g (100%), m.p. 167° to 169°C. Recrystallization from benzene (20 ml) affords a white solid m.p. 167° to 168°C.

Workup

  1. customan exotherm (ca. 50°C)
  2. customAfter the reaction subsides
  3. temperaturethe reaction mixture is refluxed for 2 hours
  4. temperatureThe reaction mixture is cooled slightly
  5. filtrationfiltered
  6. customto remove the catalyst

Sources & evidence

ORD record
ord-e39946b8906e449da315e0f2fc9c4fbf
Source dataset
uspto-grants-1976_06
Patent number
US03963742

Reaction notes

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