HCID 67223792, compound → HCID 86621502, compound

HRID 500132Notes

Reaction equation

HRID 500132 reaction equation
C[O:2][CH:3](OC)[CH2:4][S: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]([S:5][CH2:4][CH:3]=[O:2])=[CH:15][CH:14]=2)[CH:9]=[CH:10][CH:11]=1

Participants

4

Reactant 1

HCID 67223792HCID 67223792, compound

Product 1

HCID 86621502HCID 86621502, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

6-[(2,2-Dimethoxyethyl)thio]quinoline (1.0 g) was dissolved in aqueous 1N hydrochloric acid (6 mL) and acetone (3 mL). The reaction mixture was refluxed for 3 h. Acetone was removed under reduced pressure. The aqueous layer was neutralized with saturated sodium bicarbonate and extracted with ethyl acetate. The organic extracts were dried over sodium sulfate, filtered, and concentrated. The residue was purified by chromatography on silica gel with 20% ethyl acetate in hexanes to afford the desired product. LCMS: (M+H)=204.0; (M+H2O)=221.9; (M+MeOH)=236.0.

Workup

  1. temperatureThe reaction mixture was refluxed for 3 h
  2. customAcetone was removed under reduced pressure
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by chromatography on silica gel with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6067eecc97b6496a88a907870cc5cea2
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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