Iodoethane → 1-ethyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

HRID 1095357Notes

Reaction equation

HRID 1095357 reaction equation
[C:1]1([N:7]2[C:19](=O)[C:18]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[NH:11][CH2:10][C:9]=3[NH:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[O:21]1CCCC1.C([Li])C[CH2:28][CH3:29].ICC>C(#N)C>[CH2:28]([C:19]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:8]=[C:9]2[C:18]=1[C:17]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:11][C:10]2=[O:21])[CH3:29]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8028TetrahydrofuranHCID 57454660HCID 57454660, compoundHCID 178418339Butyllithium

Product 1

HCID 574462221-ethyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

Under a nitrogen atmosphere, a mixture of 2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinoline-one (3.0 g, 11.5 mmol), N,N,N′-tetramethylethylenediamine (7.7 mL), and tetrahydrofuran (128 mL) was chilled to 0° C. A solution of n-butyllithium in hexanes (12.0 mL of 2.86 M) was added dropwise. After the addition was complete the reaction mixture was stirred for 5 minutes at 0° C. and then cooled to −78° C. To the cooled solution was added iodoethane (5.3 mL, 34 mmol). The reaction mixture was warmed to ambient temperature and stirred for 30 minutes before quenching with saturated aqueous ammonium chloride. The layers were separated and the organic layer was concentrated under reduced pressure to afford a yellow oil. The yellow oil was stirred in acetonitrile and filtered to provide material that was recrystallized from methanol to provide 100 mg of 1-ethyl-2-phenyl-2,5-dihydro-4H-pyrazolo[3,4-c]quinolin-4-one as colorless needles., mp 331-334° C. MS (APCI) m/z 290 (M+H)+; Anal. calcd for C18H15N3O: C, 74.72; H, 5.23; N, 14.52. Found: C, 74.51; H, 4.96; N, 14.62.

Workup

  1. additionAfter the addition
  2. temperaturecooled to −78° C
  3. temperatureThe reaction mixture was warmed to ambient temperature
  4. stirringstirred for 30 minutes
  5. custombefore quenching with saturated aqueous ammonium chloride
  6. customThe layers were separated
  7. concentrationthe organic layer was concentrated under reduced pressure
  8. customto afford a yellow oil
  9. filtrationfiltered
  10. customto provide material that
  11. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-9e04b07e0aea46499e953b01d132571f
Source dataset
uspto-grants-2012_03
Patent number
US08138173B2

Reaction notes

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