Iodoethane → HCID 66781363, compound

HRID 1095374Notes

Reaction equation

HRID 1095374 reaction equation
[C:1]([N:5]1[CH:17]=[C:16]2[C:7]([C:8](=[O:18])[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=32)=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CN(C)[CH2:21][CH2:22]N(C)C.C([Li])CCC.C(I)C>C(OCC)(=O)C.C1COCC1>[C:1]([N:5]1[C:17]([CH2:21][CH3:22])=[C:16]2[C:7]([C:8](=[O:18])[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=32)=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 10776486HCID 10776486, compoundHCID 178418339Butyllithium

Product 1

HCID 66781363HCID 66781363, compoundYield 91.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a round-bottomed flask containing 2-tert-butyl-2,5-dihydropyrazolo[3,4-c]quinolin-4-one (20.0 g, 82.99 mmol) was added THF (500 mL) followed by N,N,N′,N′-tetramethylethylenediamine (48.13 g, 414.94 mmol). The reaction was stirred under a nitrogen atmosphere in an ice bath. To this suspension n-butyl lithium (2.5 M in hexanes, 130.0 mL, 324.91 mmol) was added dropwise. The reaction mixture was stirred in the ice bath for 2 minutes and then ethyl iodide (258.38 g, 1.66 mol) was added to the reaction. The reaction was stirred in the ice bath for 10 minutes and then the ice bath was removed. The reaction was stirred at ambient temperature overnight. Methanol (60 mL) was carefully added to quench the reaction and the solvent was evaporated to afford a dark oil. The oil was taken up in ethyl acetate (800 mL) and the organic layer was washed with water (3×600 mL). The organic layer was separated, dried (MgSO4), filtered, and evaporated to afford 2-tert-butyl-1-ethyl-2,5-dihydro-pyrazolo[3,4-c]quinolin-4-one (20.4 g) as a brown solid. A portion of this solid (15.2 g) was transferred to a round-bottomed flask and concentrated hydrochloric acid (410 mL) was added. The reaction was heated to 120° C. for 1 hour and then stirred at ambient temperature overnight. The solids in the reaction mixture were separated by filtration and washed with water. The solids were transferred to a round-bottomed flask and stirred in diethyl ether (100 mL) for 15 minutes. The product was isolated by filtration to afford 1-ethyl-2,5-dihydro-pyrazolo[3,4-c]quinolin-4-one as the hydrochloride salt. The product was stirred in 2N sodium hydroxide (60 mL) for 1.5 hours, filtered, washed with diethyl ether (600 mL), and dried under reduced pressure to afford 1-ethyl-2,5-dihydro-pyrazolo[3,4-c]quinolin-4-one as a tan brown solid (4.23 g).

Workup

  1. customthe ice bath was removed
  2. stirringThe reaction was stirred at ambient temperature overnight
  3. additionMethanol (60 mL) was carefully added
  4. customto quench
  5. customthe reaction
  6. customthe solvent was evaporated
  7. customto afford a dark oil
  8. washthe organic layer was washed with water (3×600 mL)
  9. customThe organic layer was separated
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customevaporated

Sources & evidence

ORD record
ord-f695e86f6f96473f919b7d5532a6ad11
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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