Tetrahydrofuran → HCID 19592587, compound

HRID 613499Notes

Reaction equation

HRID 613499 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][CH:20]=[C:19]([Cl:23])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13](C=O)=[CH:12]2)=[O:5].CS(CSC)=O.C[C:31]([CH3:34])([O-:33])C.[K+].[Cl-].[NH4+].[O:38]1CC[CH2:40][CH2:39]1>>[Cl:23][C:19]1[CH:20]=[CH:21][CH:22]=[C:2]([Cl:1])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][CH:10]=[C:11]2[C:16]=1[N:15]=[CH:14][C:13]([CH2:40][C:39]([O:33][CH2:31][CH3:34])=[O:38])=[CH:12]2)=[O:5]

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 99129Methyl (methylsulfinyl)methyl sulfideHCID 19592377HCID 19592377, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 19592587HCID 19592587, compound

Procedure

To a mixture of 8-(2,6-dichlorobenzoylamino)-3-formylquinoline (700 mg) and methyl methylsulfinylmethyl sulfide (302 mg) in tetrahydrofuran was added potassium tert-butoxide (501 mg) at 4° C., and the mixture was stirred for 30 minutes at the same temperature and then refluxed for 1.5 hours. The mixture was poured into cold saturated ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. A mixture of the obtained residue in dichloromethane (3 ml) and 34% solution of hydrogen chloride in ethanol (5 ml) was stirred for 2 hours at ambient temperature. The mixture was concentrated in vacuo, and the residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane) to give 8-(2,6-dichlorobenzoylamino)-3-(ethoxycarbonylmethyl)quinoline (329 mg).

Workup

  1. temperaturerefluxed for 1.5 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. additionA mixture of the obtained residue in dichloromethane (3 ml)
  7. stirring34% solution of hydrogen chloride in ethanol (5 ml) was stirred for 2 hours at ambient temperature
  8. concentrationThe mixture was concentrated in vacuo
  9. customthe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  10. washThe organic layer was washed with brine
  11. dry with materialdried over magnesium sulfate
  12. customevaporated in vacuo
  13. customThe residue was purified by column chromatography on silica gel (ethyl acetate-n-hexane)

Sources & evidence

ORD record
ord-02990caf119f4004a36615352bcf0dee
Source dataset
uspto-grants-1999_12
Patent number
US06008230

Reaction notes

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