Benzene → HCID 11298596, compound

HRID 1354202Notes

Reaction equation

HRID 1354202 reaction equation
[I-].C[S+](C)C.[OH-].[K+].[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[CH:20]=[O:21].[CH:22]1C=CC=CC=1>C(#N)C.O>[CH3:8][O:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[N:16]=[CH:15][CH:14]=[C:13]2[CH:20]1[CH2:22][O:21]1

Participants

7

Reactant 4

HCID 241BenzeneHCID 14797Potassium HydroxideHCID 75127Trimethylsulfonium iodideHCID 2193126-methoxyquinoline-4-carbaldehyde

Product 1

HCID 11298596HCID 11298596, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

Trimethylsulphonium iodide (0.954 g, 4.67 mmol) and potassium hydroxide powder (1.8 g, 32 mmol) were added to a solution of 6-methoxy-quinoline-4-carbaldehyde (0.85 g, 4.54 mmol) in acetonitrile (13.5 ml) and water (6 drops). The reaction mixture was heated at 60° C. for one hour. The mixture was then cooled to room temperature and benzene (40 ml) was added. The precipitate was filtered off and the filtrate was concentrated to dryness by rotary evaporation. The residue was diluted with water (100 ml) and ethyl acetate (100 ml), the phases were separated, and the aqueous phase was extracted twice using 50 ml of ethyl acetate each time. The combined organic phases were dried over MgSO4, filtered and concentrated to dryness by rotary evaporation. The residue was purified by column chromatography on silica gel (EtOAc).

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. filtrationThe precipitate was filtered off
  3. concentrationthe filtrate was concentrated to dryness by rotary evaporation
  4. additionThe residue was diluted with water (100 ml) and ethyl acetate (100 ml)
  5. customthe phases were separated
  6. extractionthe aqueous phase was extracted twice
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness by rotary evaporation
  10. customThe residue was purified by column chromatography on silica gel (EtOAc)

Sources & evidence

ORD record
ord-a58aa0c01b634996be0b55141b9757e8
Source dataset
uspto-grants-2007_05
Patent number
US07223776B2

Reaction notes

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