Acetic Acid → Methyl 3-quinolinecarboximidate

HRID 1588557Notes

Reaction equation

HRID 1588557 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-87a08e43c16d48a9b523ac9ff4bc1518
Source dataset
uspto-grants-1993_06
Patent number
US05223508

Reaction notes

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