Aniline → 6-Bromo-4-hydroxy-3-(phenylamino)quinolin-2(1H)-one

HRID 520848Notes

Reaction equation

HRID 520848 reaction equation
FC(F)(F)S([O-])(=O)=O.[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[C:14]([I+]C1C=CC=CC=1)=[C:13]2[OH:28].[NH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)Cl>[Br:9][C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][CH:19]=1)[NH:16][C:15](=[O:20])[C:14]([NH:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[C:13]2[OH:28]

Participants

4

Reactant 2

HCID 6115AnilineHCID 86715456(6-Bromo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)(phenyl) iodoniumtrifluoromethane sulfonate2×

Product 1

HCID 867154586-Bromo-4-hydroxy-3-(phenylamino)quinolin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (6-bromo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)(phenyl)iodoniumtrifluoromethane sulfonate (1.40 g, 2.36 mmol, Intermediate 8, step b) and aniline (1 mL) was stirred for 4 hours at room temperature. To this was added DCM and the resulting suspension was filtered. The solid was washed first with DCM followed by water and air dried under vacuum at 50° C. to yield the title compound.

Workup

  1. filtrationthe resulting suspension was filtered
  2. washThe solid was washed first with DCM
  3. customdried under vacuum at 50° C.

Sources & evidence

ORD record
ord-24bf5f5f59624fb3bf2cb0689e3133b2
Source dataset
uspto-grants-2016_05
Patent number
US09328095B2

Reaction notes

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