Thioanisole → HCID 135788287, compound

HRID 1822830Notes

Reaction equation

HRID 1822830 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([Cl:22])=[C:14]([C:19]([NH2:21])=[O:20])[CH:15]=[N:16]2)=[CH:11][C:10]=1[O:23][CH3:24])C1C=CC=CC=1.C1(SC)C=CC=CC=1>C(O)(C(F)(F)F)=O>[Cl:22][C:13]1[C:12]2[C:17](=[CH:18][C:9]([OH:8])=[C:10]([O:23][CH3:24])[CH:11]=2)[N:16]=[CH:15][C:14]=1[C:19]([NH2:21])=[O:20]

Participants

4

Reactant 2

HCID 7520ThioanisoleHCID 22170228HCID 22170228, compound

Product 1

HCID 135788287HCID 135788287, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of 7-Benzyloxy-4-chloro-6-methoxy-3-quinolinecarboxamide (1.0 g, 2.9 mmol) prepared analogous to the method described in Example 1 and thioanisole (1.75 ml, 14.1 mmol) in TFA (15 ml) was refluxed for three hours. After cooling, the solvents were removed at reduced pressure and the residue was poured on water and alkalized with aqueous ammonia. The precipitate was filtered, washed with water and dried affording 0.52 g (72% yield) of the title compound.

Workup

  1. customprepared analogous to the method
  2. temperaturewas refluxed for three hours
  3. temperatureAfter cooling
  4. customthe solvents were removed at reduced pressure
  5. additionthe residue was poured on water
  6. filtrationThe precipitate was filtered
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-6a0ddd7006574960b70990bde95b07f0
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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