Sodium hydrosulfide → HCID 19075074, compound

HRID 965003Notes

Reaction equation

HRID 965003 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[N:5]=[CH:4][CH:3]=1.[SH-:14].[Na+]>C(O)C>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11]([C:2](=[S:14])[CH:3]=[CH:4][NH:5]2)=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 28015Sodium hydrosulfideHCID 106078294-Chloro-7-methoxyquinoline

Product 1

HCID 19075074HCID 19075074, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Chloro-7-methoxyquinoline(965 mg, 5 mmol) and 70% sodium hydrosulfide (800 mg, 10 mmol) were added to ethanol (100 ml) and stirred at room temperature for 6 days. Ethanol was removed under reduced pressure from the reaction mixture. The residue was chromatographed by silica gel column chromatography, eluted with mixed solution of methylene chloride with methanol (16 : 1) for collection of yellow bands. The solvent was removed and the residue was added with a small amount of methylene chloride. The resulting precipitates were collected by filtration to obtain 590 mg (62%) of the titled compound. This compound was completely the same as the compound 1 obtained in the Example 1.

Workup

  1. customEthanol was removed under reduced pressure from the reaction mixture
  2. customThe residue was chromatographed by silica gel column chromatography
  3. washeluted with mixed solution of methylene chloride with methanol (16 : 1) for collection of yellow bands
  4. customThe solvent was removed
  5. additionthe residue was added with a small amount of methylene chloride
  6. customThe resulting precipitates
  7. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-5e0005e11f644eaa84e021cfe8c72414
Source dataset
uspto-grants-1998_06
Patent number
US05773449

Reaction notes

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