Thioanisole → HCID 135829388, compound

HRID 1433619Notes

Reaction equation

HRID 1433619 reaction equation
C1(SC)C=CC=CC=1.C([O:16][C:17]1[CH:26]=[C:25]2[C:20]([C:21]([O:27][C:28]3[CH:33]=[CH:32][C:31]([N+:34]([O-:36])=[O:35])=[CH:30][CH:29]=3)=[CH:22][CH:23]=[N:24]2)=[CH:19][C:18]=1[O:37][CH3:38])C1C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:38][O:37][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][C:17]=1[OH:16])[N:24]=[CH:23][CH:22]=[C:21]2[O:27][C:28]1[CH:29]=[CH:30][C:31]([N+:34]([O-:36])=[O:35])=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 22936514HCID 22936514, compound

Product 1

HCID 135829388HCID 135829388, compoundYield 128.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
70 °C

Procedure

After adding trifluoroacetic acid (30 ml) and thioanisole (3 ml) to 7-benzyloxy-6-methoxy-4-(4-nitrophenoxy)quinoline (4.0 g), the mixture was heated and stirred at 70° C. for 2 hours. After cooling the reaction solution, it was concentrated under reduced pressure, sodium bicarbonate water and methanol were added and the precipitated crystals were filtered out. They were then washed with diethyl ether to obtain 4.0 g of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureAfter cooling the reaction solution, it
  3. concentrationwas concentrated under reduced pressure, sodium bicarbonate water and methanol
  4. additionwere added
  5. filtrationthe precipitated crystals were filtered out
  6. washThey were then washed with diethyl ether

Sources & evidence

ORD record
ord-bc2e3684afcc4193beecbc8122157a27
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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