Thioanisole → 6-Methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolinol

HRID 1010242Notes

Reaction equation

HRID 1010242 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([S:19][C:20]3[S:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=3)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:28][CH3:29])C1C=CC=CC=1.C1(SC)C=CC=CC=1>FC(F)(F)C(O)=O>[CH3:29][O:28][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[S:19][C:20]1[S:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=1

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 589312112-{[7-(Benzyloxy)-6-methoxy-4-quinolyl]sulfanyl}-5-nitrothiophene

Product 1

HCID 1359899586-Methoxy-4-[(5-nitro-2-thienyl)sulfanyl]-7-quinolinolYield 85.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

7-(Benzyloxy)-6-methoxy-4-[(5-nitro-2-thienyl)sulfanyl]quinoline (4.0 g), trifluoroacetic acid (40 ml) and thioanisole (4 ml) were stirred together at 65° C. for 2 hours. The mixture was returned to room temperature, the solvent was distilled off under reduced pressure, 80 ml of methanol was added to the residue, and then sodium bicarbonate water was added until the foaming subsided. The precipitated solid was filtered out to obtain 2.7 g of a yellow powder.

Workup

  1. customwas returned to room temperature
  2. distillationthe solvent was distilled off under reduced pressure, 80 ml of methanol
  3. additionwas added to the residue
  4. additionsodium bicarbonate water was added until the foaming
  5. filtrationThe precipitated solid was filtered out

Sources & evidence

ORD record
ord-3791ea923c1f487aa28eff692c44372e
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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