Hydrazine hydrate (1:1) → 3,4-Diphenylpyrazole

HRID 1471885Notes

Reaction equation

HRID 1471885 reaction equation
O=[C:2]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH:4]=O.O.[NH2:19][NH2:20]>CCO>[C:12]1([C:2]2[C:3]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:4][NH:20][N:19]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 9859355HCID 9859355, compound

Product 1

HCID 3017433,4-DiphenylpyrazoleYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Oxo-2,3-diphenylpropanal (5.00 g, 22.3 mmol) was dissolved in EtOH (40 mL). Hydrazine monohydrate (2.0 mL, 38.7 mmol) was added slowly via syringe. The reaction was stirred at room temperature for an hour. The solvent was evaporated and the residue was purified by silica gel column chromatography to yield the title compound as a light purple solid (2.75 g). LCMS m/z=221.1 [M+H]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 6.99-7.57 (m, 10H), 7.66-8.09 (bs, 1H), 13.15 (bs, 1H)

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c9249aac5be4aa39b4705c058d3774b
Source dataset
uspto-grants-2015_04
Patent number
US09012478B2

Reaction notes

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