Hydrazine hydrate (1:1) → 5-phenyl-1H-pyrazolo[3,4-c]pyridin-3-amine

HRID 2213070Notes

Reaction equation

HRID 2213070 reaction equation
O.[NH2:2][NH2:3].Cl[C:5]1[C:10]([C:11]#[N:12])=[CH:9][C:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:7][CH:6]=1>N1C=CC=CC=1>[C:13]1([C:8]2[CH:9]=[C:10]3[C:11]([NH2:12])=[N:3][NH:2][C:5]3=[CH:6][N:7]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 219565045-Chloro-2-phenyl-isonicotinonitrile

Product 1

HCID 65395295-phenyl-1H-pyrazolo[3,4-c]pyridin-3-amine

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Hydrazine hydrate (0.3 mL, 5.9 mmol) was added to a stirred solution of 5-chloro-2-phenyl-isonicotinonitrile (420 mg, 1.9 mmol) in pyridine (5 mL). The reaction mixture was stirred at reflux for 3 hours, cooled and the resulting solid was filtered and dried in vacuo, affording a crude residue. Purification by column chromatography using a gradient elution of 0–5% methanol in dichloromethane as eluent afforded the title compound as a solid.

Workup

  1. temperatureat reflux for 3 hours
  2. temperaturecooled
  3. filtrationthe resulting solid was filtered
  4. customdried in vacuo
  5. customaffording a crude residue
  6. customPurification by column chromatography
  7. washa gradient elution of 0–5% methanol in dichloromethane as eluent

Sources & evidence

ORD record
ord-ff7fb349f4d04d339229e0563418d510
Source dataset
uspto-grants-2006_09
Patent number
US07105532B2

Reaction notes

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