2-Nitrophenol → HCID 2500489, compound

HRID 581181Notes

Reaction equation

HRID 581181 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].C(=O)([O-])[O-].[K+].[K+].[CH3:17][N:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19](=[O:22])[CH2:20]Br>CN(C)C=O>[CH3:17][N:18]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:19](=[O:22])[CH2:20][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 69472-NitrophenolHCID 11430Potassium CarbonateHCID 34495Acetanilide, 2-bromo-N-methyl-

Product 1

HCID 2500489HCID 2500489, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
67.5 °C

Procedure

2-Nitrophenol S7 (2.8 g), anhydrous potassium carbonate (4.1 g), and N-methyl-N-phenyl-2-bromoacetamide (4.5 g) were suspended in N,N-dimethylformamide (50 ml), and the resulting suspension was stirred at 65-70° C. for 3 hours. The reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with water and brine, then dried over anhydrous magnesium sulfate. The solvent was distilled off, obtaining 5.4 g of the compound S8.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-cb54b45bb82349408f29369222275e55
Source dataset
uspto-grants-1999_07
Patent number
US05919824

Reaction notes

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