Hydrazine hydrate (1:1) → 2-(1H-pyrazol-4-yl)pyridine

HRID 2099496Notes

Reaction equation

HRID 2099496 reaction equation
[CH:1]1[CH:6]=[C:5]([CH:7]([CH:10]=O)[CH:8]=O)[N:4]=[CH:3][CH:2]=1.O.[NH2:13][NH2:14]>C(O)C>[NH:13]1[CH:10]=[C:7]([C:5]2[CH:6]=[CH:1][CH:2]=[CH:3][N:4]=2)[CH:8]=[N:14]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 27372452-(2-Pyridyl)malondialdehyde

Product 1

HCID 35789812-(1H-pyrazol-4-yl)pyridine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Pyridyl)-malondialdehyde (7.8 g, 52 mmol) and hydrazine hydrate (3.7 mL) were heated at 75° C. in ethanol (75 mL) for 18 h. After cooling to ambient temperature and concentration in vacuo, recrystallization from EtOAc/Hexane gave 2-(1H-pyrazol-4-yl)pyridine as gold crystals. MP=136° C. 1H NMR (CD3Cl, 300 MHz) δ 6.48-8.51 (1H, m), 8.30 (1H, br. s), 8.07 (1H, br. s), 7.74 (1H, ddd), 7.68 (1H, d), 7.15 (1H, ddd). MS (ESI) 146 (M+H)+

Workup

  1. concentrationconcentration
  2. customin vacuo, recrystallization from EtOAc/Hexane

Sources & evidence

ORD record
ord-2c01509ef72f43389eb96ec7d0536408
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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