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

HRID 623973Notes

Reaction equation

HRID 623973 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 11, 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 dried in the air and 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 in the air and under vacuum at 50° C.

Sources & evidence

ORD record
ord-d23476827f4e47fe8f3ea1996d61268c
Source dataset
uspto-grants-2016_04
Patent number
US09303015B2

Reaction notes

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