HCID 67224735, compound → HCID 86621503, compound

HRID 500145Notes

Reaction equation

HRID 500145 reaction equation
C[O:2][CH:3](OC)[CH2:4][O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[N:12]=[CH:11][CH:10]=[CH:9]2>Cl.CC(C)=O>[N:12]1[C:13]2[C:8](=[CH:7][C:6]([O:5][CH2:4][CH:3]=[O:2])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 67224735HCID 67224735, compound

Product 1

HCID 86621503HCID 86621503, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

6-(2,2-dimethoxyethoxy)quinoline (9.0 g) was dissolved in aqueous 1N hydrochloric acid (60 mL) and acetone (30 mL). The reaction mixture was heated under reflux for 3 h. Acetone was removed under reduced pressure. To the residue was added ethyl acetate, and the solution was neutralized with aqueous 1N NaOH. The organic layer was washed with brine, dried over sodium sulfate, filtered, and concentrated to afford the desired product which was used in the next step without further purification. (4.8 g) LCMS: (M+H2O)=205.9, and (M+MeOH)=219.9.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux for 3 h
  3. customAcetone was removed under reduced pressure
  4. additionTo the residue was added ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e96ae5ace3a24b2cb622f60e11b267b6
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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