Acetic Acid → HCID 16723510, compound

HRID 2283907Notes

Reaction equation

HRID 2283907 reaction equation
C(Cl)(=O)C.C(O)(=O)C.C(O)(=O)C(O)=O.[CH2:15]([NH:17][NH2:18])[CH3:16].[NH:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:21]([C:28](=O)[C:29]([O:31]C)=O)=[CH:20]1>C(O)C>[CH2:15]([N:17]1[CH:20]=[C:21]2[C:28]([C:29](=[O:31])[NH:19][C:27]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=32)=[N:18]1)[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6367Acetyl chlorideHCID 96181Hydrazine, ethyl-, ethanedioate (1:1)HCID 588944Methyl 3-indoleglyoxylate

Product 1

HCID 16723510HCID 16723510, compoundYield 67.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Acetyl chloride (19 mL, 273 mmol), acetic acid (30 mL), and ethylhydrazine oxalate (41 g, 272 mmol) were added sequentially to a suspension of methyl 1H-indol-3-yl(oxo)acetate (37 g, 180 mmol) in ethanol (910 mL). The reaction mixture was heated at reflux for 18 hours, cooled to ambient temperature, and concentrated under reduced pressure to a small volume. Dichloromethane (100 mL) and ice were added, and the mixture was adjusted to pH 14 with the addition of 50% w/w sodium hydroxide. A precipitate formed. The dichloromethane was removed under reduced pressure, and the precipitate was isolated by filtration, triturated with hot acetonitrile, and isolated by filtration to provide 26 g of 2-ethyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as a tan solid.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated under reduced pressure to a small volume
  4. additionDichloromethane (100 mL) and ice were added
  5. additionthe mixture was adjusted to pH 14 with the addition of 50% w/w sodium hydroxide
  6. customA precipitate formed
  7. customThe dichloromethane was removed under reduced pressure
  8. customthe precipitate was isolated by filtration
  9. customtriturated with hot acetonitrile
  10. customisolated by filtration

Sources & evidence

ORD record
ord-e5a22517bcd64ab981ecdd21cfb8dfd0
Source dataset
uspto-grants-2015_09
Patent number
US09145410B2

Reaction notes

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