N-Methylaniline → 6-Bromo-4-hydroxy-3-(methyl(phenyl)amino)quinolin-2(1H)-one

HRID 623974Notes

Reaction equation

HRID 623974 reaction equation
[CH3:1][NH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.FC(F)(F)S([O-])(=O)=O.[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[C:22]([I+]C1C=CC=CC=1)=[C:21]2[OH:36]>>[Br:17][C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[NH:24][C:23](=[O:28])[C:22]([N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)=[C:21]2[OH:36]

Participants

3

Reactant 2

HCID 7515N-MethylanilineHCID 86715456(6-Bromo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)(phenyl) iodoniumtrifluoromethane sulfonate

Product 1

HCID 867154596-Bromo-4-hydroxy-3-(methyl(phenyl)amino)quinolin-2(1H)-one

Procedure

The title compound was prepared using N-methylaniline in place of aniline 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. customwas purified by flash column chromatography (silica gel, 50% EtOAc-Heptane)

Sources & evidence

ORD record
ord-f9f80428153e450e8e3e3d69be3c9b1e
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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