Thioanisole → HCID 135829388, compound

HRID 387960Notes

Reaction equation

HRID 387960 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-440e7ca704e34410a20706c53087c16b
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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