Phenylhydrazine → 5-Amino-3-methyl-1-phenylpyrazole

HRID 1054304Notes

Reaction equation

HRID 1054304 reaction equation
[C:1]1([NH:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NN>>[CH3:4][C:3]1[CH:2]=[C:1]([NH2:7])[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=1

Participants

3

Reactant 2

HCID 7516PhenylhydrazineHCID 9321Hydrazine

Product 1

HCID 708015-Amino-3-methyl-1-phenylpyrazoleYield 37%

Procedure

Synthesized using the procedure for 22 except phenyl hydrazine was used as the hydrazine. Recrystallization of crude from hot EtOH provided the title compound (1.28 g, 37%) as pink crystals. 1H NMR (400 MHz, CDCl3) δ 7.54 (s, 1H), 7.51 (s, 1H), 7.44 (t, J=7.5 Hz, 2H), 7.30 (t, J=7.4 Hz, 1H), 5.43 (s, 1H), 3.77 (s, 2H), 2.22 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 149.37, 145.21, 138.65, 129.38, 126.99, 123.77, 90.68, 13.93.

Workup

  1. customSynthesized
  2. customRecrystallization of crude from hot EtOH

Sources & evidence

ORD record
ord-49f7e8fc93d44d78bf769feb1931442a
Source dataset
uspto-grants-2016_07
Patent number
US09394303B2

Reaction notes

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