Potassium Carbonate → HCID 9935898, compound

HRID 1954175Notes

Reaction equation

HRID 1954175 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8](=[O:13])[C:7]([C:14]1[N:15]=[N:16][N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[CH:21]=3)[N:18]=1)=[CH:6]2.[C:38](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH3:38])[C:8](=[O:13])[C:7]([C:14]1[N:15]=[N:16][N:17]([CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH2:27][C:28]4[CH:37]=[CH:36][C:35]5[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=5)[N:29]=4)[CH:21]=3)[N:18]=1)=[CH:6]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 135484041HCID 135484041, compound

Product 1

HCID 9935898HCID 9935898, compoundYield 81.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 6-methoxy-3-{2-[3-(2-quinolylmethoxy)benzyl]tetrazolyl}quinolin-2-one (1.61 g, 3.30 mmol) and potassium carbonate (684 mg, 4.95 mmol), was added DMF (30 ml). Methyl iodinate (562 mg, 3.96 mmol) was added dropwise to the resultant mixture, and thereafter stirred for four hours at a bath temperature of 80° C. The solvent of the reaction mixture was removed under reduced pressure. Water was added to the mixture, and the organic phase was extracted therefrom with a mixture of chloroform-methanol (10:1). The organic phase was dried over sodium sulfate anhydrate, subjected to silica gel column chromatography (with chloroform-methanol (50:1)), and concentrated under reduced pressure. The resultant residue was recrystallized from a chloroform-n-hexan-ether mixture, to thereby obtain the title compound (1.35 g, 2.68 mmol, 81.1%) as pale yellow powder.

Workup

  1. customThe solvent of the reaction mixture was removed under reduced pressure
  2. additionWater was added to the mixture
  3. extractionthe organic phase was extracted
  4. additionwith a mixture of chloroform-methanol (10:1)
  5. dry with materialThe organic phase was dried over sodium sulfate anhydrate
  6. concentrationconcentrated under reduced pressure
  7. customThe resultant residue was recrystallized from a chloroform-n-hexan-ether mixture

Sources & evidence

ORD record
ord-8e222529e7264cdaa954d44ba1f43be4
Source dataset
uspto-grants-2000_09
Patent number
US06121286

Reaction notes

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