3-Quinolinecarbonitrile → Quinoline-3-carboximidamide

HRID 1822793Notes

Reaction equation

HRID 1822793 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]#[N:12])[CH:2]=1.C[Si]([N-:17][Si](C)(C)C)(C)C.[Li+]>C(OCC)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]([NH2:17])=[NH:12])[CH:2]=1

Participants

4

Reactant 2

HCID 931773-QuinolinecarbonitrileHCID 2733832Lithium Hexamethyldisilazide

Product 1

HCID 4572135Quinoline-3-carboximidamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Quinoline-3-nitrile (1.0 g) was dissolved in diethyl ether (30 mL) and treated with lithium bis(trimethylsilyl)amide (1.0 M in THF, 13 mL). The reaction was stirred for 3 hours, then washed 3 times with 1 N HCl (50 mL). The combined aqueous washes were neutralized with 6 N NaOH and extracted 6 times with ethyl acetate (50 mL). The ethyl acetate extractions were dried over sodium sulfate and the solvent was evaporated to provide 0.63 g of quinoline-3-carboxamidine.

Workup

  1. washwashed 3 times with 1 N HCl (50 mL)
  2. extractionextracted 6 times with ethyl acetate (50 mL)
  3. extractionThe ethyl acetate extractions
  4. dry with materialwere dried over sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-cc5bd5e4a26743c295bcd424ff8d1115
Source dataset
uspto-grants-2006_05
Patent number
US07037916B2

Reaction notes

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