Hydrochloric Acid → HCID 16723630, compound

HRID 1984508Notes

Reaction equation

HRID 1984508 reaction equation
[CH2:1]([N:3]1[CH:15]=[C:14]2[C:5]([C:6](=[O:16])[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=32)=[N:4]1)[CH3:2].CN(CCN(C)C)C.C([Li])CCC.Cl.CN([CH:34]=[O:35])C>C(#N)C.C1COCC1>[CH2:1]([N:3]1[C:15]([CH:34]=[O:35])=[C:14]2[C:5]([C:6](=[O:16])[NH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=32)=[N:4]1)[CH3:2]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 16723510HCID 16723510, compoundHCID 178418339Butyllithium

Product 1

HCID 16723630HCID 16723630, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a mixture of 2-ethyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one (10 g, 46.8 mmol), N,N,N,N-tetramethylethylenediamine (31 mL), and THF (520 mL) was chilled to 0° C. A solution of n-butyllithium in hexanes (56 mL of 2.5 M) was added dropwise. After the addition was complete the reaction mixture was stirred for 5 minutes and then DMF (72 mL) was added dropwise. The reaction mixture was warmed to ambient temperature and stirred for 1 hour. 1 N hydrochloric acid was added and the reaction mixture was stirred for 1 hour. The reaction mixture was concentrated under reduced pressure to about half the original volume and then diluted with water and extracted with dichloromethane. The combined extracts were dried over sodium sulfate, filtered, and then concentrated under reduced pressure to provide a dark yellow oil. The oil was combined with acetonitrile and stirred for 20 minutes. A bright yellow solid was isolated by filtration to provide 4 g of 2-ethyl-4-oxo-4,5-dihydro-2H-pyrazolo[3,4-c]quinoline-1-carbaldehyde as a yellow powder. An additional 3 g of material was isolated from the mother liquor.

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was warmed to ambient temperature
  3. stirringstirred for 1 hour
  4. stirringthe reaction mixture was stirred for 1 hour
  5. concentrationThe reaction mixture was concentrated under reduced pressure to about half the original volume
  6. additiondiluted with water
  7. extractionextracted with dichloromethane
  8. dry with materialThe combined extracts were dried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customto provide a dark yellow oil
  12. stirringstirred for 20 minutes
  13. customA bright yellow solid was isolated by filtration

Sources & evidence

ORD record
ord-0f6692fc3f4a47d29e085725f7522db3
Source dataset
uspto-grants-2009_06
Patent number
US07544697B2

Reaction notes

Loading…