Potassium Iodide → 1H-Quinoline-4-carboxylic acid, 6-methoxy-2-oxo-, ethyl ester

HRID 649520Notes

Reaction equation

HRID 649520 reaction equation
Br[C:2]([CH3:12])([CH3:11])[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].[I-].[K+].N1C=[CH:18][N:17]=[N:16]1.C(=O)([O-])[O-].[K+].[K+].[C:26](#[N:28])C>>[N:17]1([C:2]([CH3:12])([CH3:11])[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[O:4])[CH:18]=[N:28][CH:26]=[N:16]1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 66324Phenyl 2-bromo-2-propyl ketoneHCID 178418936HCID 178418936, compound

Product 1

HCID 1853191H-Quinoline-4-carboxylic acid, 6-methoxy-2-oxo-, ethyl esterYield 28%

Conditions

Temperature
75 °C

Procedure

45.4 g (0.2 mol) of α-bromoisobutyrophenone and 1 g of potassium iodide are added to 14 g (0.2 mol) of triazole and 27 g (0.2 mol) of potassium carbonate in 100 ml of acetonitrile at 75° C. When the addition has ended, the mixture is stirred at 75° C. for a further 8 hours, filtered and rinsed with acetonitrile. The filtrate is concentrated, the residue is taken up in chloroform and the mixture is washed twice with water, dried over sodium sulphate and freed from the solvent in vacuo. The residue is recrystallized from ethyl acetate/petroleum ether. 12.1 g (28% of theory) of α-(1,2,4-triazol-1-yl)-isobutyrophenone of melting point 134° C. to 135° C. are obtained.

Workup

  1. additionWhen the addition
  2. filtrationfiltered
  3. washrinsed with acetonitrile
  4. concentrationThe filtrate is concentrated
  5. washthe mixture is washed twice with water
  6. dry with materialdried over sodium sulphate
  7. customThe residue is recrystallized from ethyl acetate/petroleum ether

Sources & evidence

ORD record
ord-1b13cf87327b4cfd8e95b837bf3058e7
Source dataset
uspto-grants-1988_04
Patent number
US04740515

Reaction notes

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