Ammonia → 4-((4-Fluorobenzyl)oxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1H)-one

HRID 2202849Notes

Reaction equation

HRID 2202849 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][NH:11][C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.Br[C:18]1[CH:19]=[CH:20][C:21]([N+:26]([O-:28])=[O:27])=[C:22]([CH:25]=1)[NH:23][CH3:24].CNCCNC.C(=O)([O-])[O-].[K+].[K+].N>[Cu](I)I.CS(C)=O>[F:1][C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][C:8]2[CH:13]=[CH:12][N:11]([C:18]3[CH:19]=[CH:20][C:21]([N+:26]([O-:28])=[O:27])=[C:22]([NH:23][CH3:24])[CH:25]=3)[C:10](=[O:14])[CH:9]=2)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 8070N,N'-DimethylethylenediamineHCID 11430Potassium CarbonateHCID 106095305-bromo-N-methyl-2-nitroanilineHCID 220499004-(4-Fluorobenzyloxy)-1h-pyridin-2-one

Product 1

HCID 896904424-((4-Fluorobenzyl)oxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1H)-oneYield 75.8%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-((4-fluorobenzyl)oxy)pyridin-2(1H)-one (2.06 g), 5-bromo-N-methyl-2-nitroaniline (2.17 g), N,N′-dimethylethylenediamine (1.00 ml), copper iodide (1.79 g), potassium carbonate (3.90 g) and DMSO (30 ml) was stirred at 150° C. for 2 h. The mixture was added to 28% NH3 solution. The precipitate was collected and washed with water to give the title compound (2.63 g) as a yellow solid.

Workup

  1. customThe precipitate was collected
  2. washwashed with water

Sources & evidence

ORD record
ord-fce879045d814c4d8f7b304d8cfffe5a
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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