Hydrazine hydrate (1:1) → HCID 90092824, compound

HRID 1774579Notes

Reaction equation

HRID 1774579 reaction equation
[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4](=O)[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=O.O.[NH2:18][NH2:19]>C(O)C>[CH3:1][O:2][CH:3]([O:15][CH3:16])[C:4]1[NH:19][N:18]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH:5]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 62745196HCID 62745196, compound

Product 1

HCID 90092824HCID 90092824, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred slurry of 4,4-dimethoxy-1-(pyridin-2-yl)butane-1,3-dione (9a) (5.11 g, 22.9 mmol) in ethanol (200 mL) was dropwise added hydrazine monohydrate (1.28 mL, 26.3 mmol). The reaction mixture was stirred at room temperature overnight and concentrated in vacuo. A saturated solution of sodium hydrogenocarbonate (30 mL) was added to the residue. The aqueous layer was extracted with ethyl acetate (2×50 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo to provide 2-[5-(dimethoxymethyl)-1H-pyrazol-3-yl]pyridine (9b) (3.51 g, 16.0 mmol, 70%) which was used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. additionA saturated solution of sodium hydrogenocarbonate (30 mL) was added to the residue
  3. extractionThe aqueous layer was extracted with ethyl acetate (2×50 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-84780ec9744f47fbbaf00e142d6d42e8
Source dataset
uspto-grants-2016_02
Patent number
US09260395B2

Reaction notes

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