Acetic Acid → Methyl 3-quinolinecarboximidate

HRID 327128Notes

Reaction equation

HRID 327128 reaction equation
[C:1]([C:3]1[CH:4]=[N:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)#[N:2].C[O-].[Na+].[C:16](O)(=[O:18])C>CO>[N:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:12]=[C:3]([C:1](=[NH:2])[O:18][CH3:16])[CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 931773-QuinolinecarbonitrileHCID 10942334Sodium Methoxide

Product 1

HCID 19734518Methyl 3-quinolinecarboximidate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-cyanoquinoline (1.58 g, 10.2 mmol) was dissolved in methanol (20 ml), and sodium methoxide (0.06 g, 1.1 mmol) was added. The reaction was conducted at room temperature for 22 hours. After the reaction was completed, acetic acid (0.07 g, 1.1 mmol) was added to neutralize the reaction solution, and the solution was concentrated under reduced pressure. Diethyl ether (60 ml) was added to the concentrated residue, and insolubles were removed by filtration. The filtrate was concentrated under reduced pressure to give the crude product of methyl 3-quinolinecarboximidate.

Workup

  1. concentrationthe solution was concentrated under reduced pressure
  2. additionDiethyl ether (60 ml) was added to the concentrated residue, and insolubles
  3. customwere removed by filtration
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-805c66f067644aaa964d24fc0ffbae3e
Source dataset
uspto-grants-1993_12
Patent number
US05272164

Reaction notes

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