Hydrazine hydrate (1:1) → HCID 178434440, compound

HRID 1397080Notes

Reaction equation

HRID 1397080 reaction equation
Cl[C:2]1[C:7]([C:8](=O)[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>C(O)CCC>[CH3:9][C:8]1[C:7]2[C:2](=[N:3][CH:4]=[CH:5][CH:6]=2)[NH:13][N:12]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 109426973-Acetyl-2-chloropyridine

Product 1

HCID 178434440HCID 178434440, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To a solution of 1-(2-Chloropyridin-3-yl)ethanone (III) (0.311 g, 2 mmol) in n-butanol (10 mL) was added hydrazine hydrate (1.45 mL, 30 mmol). The reaction was refluxed overnight. The solution was cooled and the solvent was evaporated under vacuum. The residue was dissolved in DCM and washed successively by water and brine. The organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give 3-methyl-1H-pyrazolo[3,4-b]pyridine (IV) as a white solid (192 mg, 1.44 mmol, 72% yield). 1H NMR (CDCl3) δ ppm 2.64 (s, 3H), 7.14 (dd, J=8.01, 4.62 Hz, 1H), 8.14 (dd, J=7.54, 1.88 HZ, 1H), 8.59 (dd, J=4.52, 1.32 HZ, 1H), 11.68 (brs, 1H).

Workup

  1. temperatureThe reaction was refluxed overnight
  2. temperatureThe solution was cooled
  3. customthe solvent was evaporated under vacuum
  4. dissolutionThe residue was dissolved in DCM
  5. washwashed successively by water and brine
  6. dry with materialThe organic layers were dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d03828f38f444a69a00bc2d0df4f0a03
Source dataset
uspto-grants-2014_12
Patent number
US08901150B2

Reaction notes

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