Ammonia → 4-(4-Chlorobenzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1h)-one

HRID 2202913Notes

Reaction equation

HRID 2202913 reaction equation
[Cl: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>[Cl: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 574978644-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-one

Product 1

HCID 896911684-(4-Chlorobenzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1h)-oneYield 73.3%

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (10 g), 5-bromo-N-methyl-2-nitroaniline (9.80 g), N,N′-dimethylethylenediamine (4.76 ml), copper iodide (8.08 g), potassium carbonate (17.59 g) and DMSO (200 ml) was heated at 150° C. for 2 h. The mixture was poured into 28% NH3 solution. The resulting precipitate was collected and washed with IPA. The solid was dissolved in DMSO (100 ml) at 80° C., and allowed to cool to room temperature to give a precipitate. After filtration, the precipitate was washed with IPA and dried to give the title compound (12 g) as a yellow solid.

Workup

  1. customThe resulting precipitate was collected
  2. washwashed with IPA
  3. dissolutionThe solid was dissolved in DMSO (100 ml) at 80° C.
  4. temperatureto cool to room temperature
  5. customto give a precipitate
  6. filtrationAfter filtration
  7. washthe precipitate was washed with IPA
  8. customdried

Sources & evidence

ORD record
ord-982af0a26e344a98bac3ee14ed7821f9
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

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