Acetic Acid → 2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

HRID 1095347Notes

Reaction equation

HRID 1095347 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5](O)(=O)[CH3:6].[C:9]1([NH:15][NH2:16])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)C>[C:9]1([N:15]2[CH:6]=[C:5]3[C:2]([C:1](=[O:3])[NH:15][C:9]4[CH:10]=[CH:11][CH:12]=[CH:13][C:14]=43)=[N:16]2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6367Acetyl chlorideHCID 7516Phenylhydrazine

Product 1

HCID 49628662-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (26 mL, 364 mmol), acetic acid (30 mL), and phenylhydrazine (36 mL, 364 mmol) were added sequentially to a suspension of material from Part A (37 g, 182 mmol) in ethanol (910 mL). The reaction mixture was heated at reflux for 18 hours. A white solid was isolated by filtration and washed with ethanol. Analysis of this material by 1H NMR indicated that this material was a 1:1 mixture of starting material and product. The solid was triturated with refluxing acetonitrile to provide 2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as a white powder, mp>250° C. MS (APCI) m/z 262 (M+H)+; Anal. calcd for C16H11N3O: C, 73.55; H, 4.24; N, 16.08. Found: C, 73.44; H, 4.21; N, 16.20.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. customA white solid was isolated by filtration
  4. washwashed with ethanol
  5. additiona 1:1 mixture of starting material and product
  6. customThe solid was triturated with refluxing acetonitrile

Sources & evidence

ORD record
ord-fdb21a5aa3fd4161b3474d58f8e28f0b
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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