Hydrazine → HCID 178509226, compound

HRID 390532Notes

Reaction equation

HRID 390532 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[NH2:10][NH2:11].O1CCOCC1>C(OCC)(=O)C>[NH:10]1[C:2]2=[N:3][CH:4]=[CH:5][CH:6]=[C:7]2[C:8]([NH2:9])=[N:11]1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 312751,4-DioxaneHCID 810792-Chloronicotinonitrile

Product 1

HCID 178509226HCID 178509226, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

2-Chloro-3-cyanopyridine (2.77 g), hydrazine (5 mL), and dioxane (100 mL) were combined in a sealed tube and heated at 150° C. for 16 hr. The reaction mixture was cooled to room temperature and concentrated in vacuo to provide a crude residue. The resultant residue was dissolved in ethyl acetate (100 mL) and washed with saturated NaCl solution (50 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo to afford 1H-pyrazolo[3,4-b]pyridin-3-ylamine as a yellow solid which was used without further purification.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated in vacuo
  3. customto provide a crude residue
  4. washwashed with saturated NaCl solution (50 mL)
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0d57d7b0e1ae4d30934a9502f610a4bd
Source dataset
uspto-grants-2013_02
Patent number
US08383630B2

Reaction notes

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