Acetic Acid → Methyl 3-quinolinecarboximidate

HRID 374182Notes

Reaction equation

HRID 374182 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-e3375ed382f2409f97ed00b2d5b32f62
Source dataset
uspto-grants-1992_11
Patent number
US05166347

Reaction notes

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