N-Ethylaniline → 6-Bromo-3-(ethyl(phenyl)amino)-4-hydroxyquinolin-2(1H)-one

HRID 623975Notes

Reaction equation

HRID 623975 reaction equation
[CH2:1]([NH:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:2].FC(F)(F)S([O-])(=O)=O.[Br:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[C:23]([I+]C1C=CC=CC=1)=[C:22]2[OH:37]>>[Br:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[NH:25][C:24](=[O:29])[C:23]([N:3]([CH2:1][CH3:2])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[C:22]2[OH:37]

Participants

3

Reactant 2

HCID 7670N-EthylanilineHCID 86715456(6-Bromo-4-hydroxy-2-oxo-1,2-dihydroquinolin-3-yl)(phenyl) iodoniumtrifluoromethane sulfonate

Product 1

HCID 867154606-Bromo-3-(ethyl(phenyl)amino)-4-hydroxyquinolin-2(1H)-one

Procedure

The title compound was prepared using N-ethylaniline 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-7cf644638eaa42d2960f792c10d0bc93
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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