Thioanisole → HCID 23498073, compound

HRID 1837343Notes

Reaction equation

HRID 1837343 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][C:18]=1[O:19][CH2:20][CH2:21][O:22][CH3:23])[N:15]=[CH:14][C:13]([C:24]#[N:25])=[C:12]2[Cl:26])C1C=CC=CC=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[Cl:26][C:12]1[C:11]2[C:16](=[CH:17][C:18]([O:19][CH2:20][CH2:21][O:22][CH3:23])=[C:9]([OH:8])[CH:10]=2)[N:15]=[CH:14][C:13]=1[C:24]#[N:25]

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 23498112HCID 23498112, compound

Product 1

HCID 23498073HCID 23498073, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 6-benzyloxy-4-chloro-7-(2-methoxyethoxy)-3-quinolinecarbonitrile (512 mg, 1.39 mmol) and 0.9 mL of thioanisole in 7.5 mL of trifluoroacetic acid is heated at reflux for 3 hours then concentrated in vacuo. The residue is treated with ice water and then basified to pH 9-10 by the addition of aqueous ammonium hydroxide. The resultant suspension is extracted with ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. Trituration with diethyl ether provides 302 mg of 4-chloro-6-hydroxy-7-(2-methoxyethoxy)-3-quinolinecarbonitrile, mp 174-175° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 3 hours
  3. concentrationthen concentrated in vacuo
  4. additionThe residue is treated with ice water
  5. additionbasified to pH 9-10 by the addition of aqueous ammonium hydroxide
  6. extractionThe resultant suspension is extracted with ethyl acetate
  7. washThe organic layer is washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff8f28eaa64d41efb52bc8b88d0a1899
Source dataset
uspto-grants-2004_08
Patent number
US06780996B2

Reaction notes

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