Aniline → 6-Bromo-4-hydroxy-3-(isopropyl(phenyl)amino)quinolin-2(1H)-one

HRID 623976Notes

Reaction equation

HRID 623976 reaction equation
[CH:1]([NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)([CH3:3])[CH3:2].NC1C=CC=CC=1.FC(F)(F)S([O-])(=O)=O.[Br:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])[C:31]([I+]C1C=CC=CC=1)=[C:30]2[OH:45]>>[Br:26][C:27]1[CH:28]=[C:29]2[C:34](=[CH:35][CH:36]=1)[NH:33][C:32](=[O:37])[C:31]([N:4]([CH:1]([CH3:3])[CH3:2])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[C:30]2[OH:45]

Participants

4

Reactant 3

HCID 6115AnilineHCID 13032N-IsopropylanilineHCID 86715456(6-Bromo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)(phenyl) iodoniumtrifluoromethane sulfonate

Product 1

HCID 867154616-Bromo-4-hydroxy-3-(isopropyl(phenyl)amino)quinolin-2(1H)-one

Procedure

The title compound was prepared using N-isopropylaniline at 50° C. in place of aniline at room temperature according to the procedure of Intermediate 11, step c except the crude solid was purified by flash column chromatography (silica gel, 50% EtOAc-Heptane), affording the title compound.

Workup

  1. customThe title compound was prepared
  2. customat 50° C.
  3. customat room temperature
  4. customwas purified by flash column chromatography (silica gel, 50% EtOAc-Heptane)

Sources & evidence

ORD record
ord-b82909726f8c4d47a492ec43f530b0e0
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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