Hydrochloric Acid → 2-(1H-pyrazol-1-yl)pyridine

HRID 2099499Notes

Reaction equation

HRID 2099499 reaction equation
[NH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1)[NH2:2].Cl.[C:10]([O-])(O)=O.[Na+].[CH3:15][CH2:16]O>O.CCOC(C)=O>[N:1]1([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=2)[CH:15]=[CH:16][CH:10]=[N:2]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 786452-HydrazinopyridineHCID 516892Sodium Bicarbonate

Product 1

HCID 53240862-(1H-pyrazol-1-yl)pyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Hydrazinopyridine (7.6 g, 70 mmol), malondialdehyde-bis-(dimethylacetal) (11.5 mL, 70 mmol) and HCl (10 M, 7 mL) in EtOH (100 mL) were heated at 75° C. After 2 h, the resulting reaction mixture was cooled to ambient temperature and concentrated in vacuo to a give a brown solid. This was suspended in H2O (100 mL) and EtOAc (100 mL), and NaHCO3 added until there was no further effervescence. The EtOAc layer was then separated and the aqueous layer shaken with EtOAc (3×100 mL). The combined organic layers were dried over Na2SO4 and concentrated to afford 2-(1H-pyrazol-1-yl)pyridine as a brown oil which was used without further purification. MS (ESI) 147 (M+H)+

Workup

  1. customthe resulting reaction mixture
  2. concentrationconcentrated in vacuo to
  3. customa give a brown solid
  4. customThe EtOAc layer was then separated
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8398d2fefba545eb94c1ef32027f2a67
Source dataset
uspto-grants-2009_08
Patent number
US07569592B2

Reaction notes

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