Acetic Acid → 3-amino-5,6-dihydro-6-p-tolyl-1H-pyrazolo[3,4-c]pyridin-7(4H)-one

HRID 390001Notes

Reaction equation

HRID 390001 reaction equation
[O:1]=[C:2]1[C:7](=O)[CH:6]([C:9]#[N:10])[CH2:5][CH2:4][N:3]1[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=1.Cl.[NH2:19][NH2:20].C(O)(=O)C>C(O)C>[NH2:10][C:9]1[C:6]2[CH2:5][CH2:4][N:3]([C:11]3[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=3)[C:2](=[O:1])[C:7]=2[NH:20][N:19]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 115031Hydrazinium chlorideHCID 679973142,3-Dioxo-1-p-tolylpiperidine-4-carbonitrile

Product 1

HCID 679969973-amino-5,6-dihydro-6-p-tolyl-1H-pyrazolo[3,4-c]pyridin-7(4H)-oneYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

2,3-Dioxo-1-p-tolylpiperidine-4-carbonitrile (3.56 g, 15.597 mmol) was added to anhydrous ethanol (52.0 mL) and dissolved by heating to 60° C. After adding hydrazine hydrochloride (1.06 mL, 21.836 mmol) and glacial acetic acid (1.34 mL, 23.396 mmol) room temperature, reaction was carried out for 2 days. After removing ethanol by distillation, the produced solid was filtered and then acetic acid was completely removed by washing with NaHCO3 twice or more times. A target compound (3.25 g, 13.414 mmol, 86.0%) was yielded as white solid.

Workup

  1. dissolutiondissolved
  2. additionAfter adding
  3. customAfter removing ethanol
  4. distillationby distillation
  5. filtrationthe produced solid was filtered
  6. customacetic acid was completely removed
  7. washby washing with NaHCO3 twice

Sources & evidence

ORD record
ord-cf875ff17b274de9991888eeaacf2388
Source dataset
uspto-grants-2013_02
Patent number
US08383631B2

Reaction notes

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