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

HRID 853378Notes

Reaction equation

HRID 853378 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 bicarnobate 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 bicarnobate water was added until the foaming
  5. filtrationThe precipitated solid was filtered out

Sources & evidence

ORD record
ord-d2d75124c25d4d5ca0d7a0c601777600
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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