Acetic Acid → HCID 16723510, compound

HRID 1095343Notes

Reaction equation

HRID 1095343 reaction equation
C(Cl)(=O)C.C(O)(=O)C.[CH2:9]([NH:11][NH2:12])[CH3:10].[NH:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([C:22](=O)[C:23]([O:25]C)=O)=[CH:14]1>C(O)C>[CH2:9]([N:11]1[CH:14]=[C:15]2[C:22]([C:23](=[O:25])[NH:13][C:21]3[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=32)=[N:12]1)[CH3:10]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6367Acetyl chlorideHCID 29062EthylhydrazineHCID 588944Methyl 3-indoleglyoxylate

Product 1

HCID 16723510HCID 16723510, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (0.7 mL, 9.8 mmol), acetic acid (1 mL), and ethylhydrazine (1.5 g, 9.8 mmol) were added sequentially to a suspension of methyl (1H-indol-3-yl)glyoxalate (1.0 g, 4.9 mmol) in ethanol (25 mL). The reaction mixture was heated at reflux for 18 hours. The reaction mixture was cooled to ambient temperature and then concentrated under reduced pressure. The residue was combined with acetonitrile. A pink solid was isolated by filtration and then purified by automated flash chromatography (Biotage, eluted with a gradient of 0-30% CMA in chloroform) to provide a white solid. This material was recrystallized from acetonitrile to provide 360 mg of 2-ethyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as white crystals, mp>250° C. MS (APCI) m/z 214 (M+H)+; Anal. calcd for C12H11N3O: C, 67.59; H, 5.20; N, 19.71. Found: C, 67.52; H, 5.14; N, 19.90.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. customA pink solid was isolated by filtration
  5. custompurified by automated flash chromatography (Biotage
  6. washeluted with a gradient of 0-30% CMA in chloroform)
  7. customto provide a white solid
  8. customThis material was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-dbb42cdfc7c849afbdcebaff2d4e491d
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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