2-Nitrophenol → HCID 18757072, compound

HRID 434111Notes

Reaction equation

HRID 434111 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])([O-:3])=[O:2].[H-].[Na+].[H][H].[CH2:15]([N:22]([CH2:36][CH2:37]Cl)[CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C)C=O>[CH2:15]([N:22]([CH2:36][CH2:37][O:10][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:23][CH2:24][CH2:25][CH2:26][NH:27][C:28](=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 69472-NitrophenolHCID 24758Sodium hydrideHCID 15840796HCID 15840796, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18757072HCID 18757072, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
67.5 °C

Procedure

2-nitrophenol (0.56 g, 0.004 mole) is added in portions to a stirred suspension of sodium hydride (160 mg of a dispersion at 60% in oil, 0.004 mole) in dry dimethylformamide (10 ml) in a nitrogen atmosphere. When the hydrogen evolution is completed, while stirring, a solution of N-[4-{benzyl (2-chloroethyl)amino}butyl]benzamide (1.6 g, 0.0046 mole) in dry dimethylformamide (5 ml) is added dropwise. The reaction mixture is heated to 65-70 degrees C. for 1.5 hours, cooled back to ambient temperature, and poured over crushed ice. The mixture is extracted with ether (50 ml); the organic phase is separated and washed with water (3×20 ml) before being dried over magnesium sulfate. Filtration and evaporation of the solvent at reduced pressure yield 1.3 g of an oil which is purified by flash chromatography over silica gel by using a mixture of ethyl acetate/heptane (3/1) as eluant. The expected compound is obtained in the form of oil (0.94 g, 52%).

Workup

  1. temperaturecooled back to ambient temperature
  2. additionpoured
  3. customover crushed ice
  4. extractionThe mixture is extracted with ether (50 ml)
  5. customthe organic phase is separated
  6. washwashed with water (3×20 ml)
  7. dry with materialbefore being dried over magnesium sulfate
  8. filtrationFiltration and evaporation of the solvent at reduced pressure yield 1.3 g of an oil which
  9. customis purified by flash chromatography over silica gel
  10. additiona mixture of ethyl acetate/heptane (3/1) as eluant

Sources & evidence

ORD record
ord-1a6fdf9a5a4244cab2bdfdb9ed0e496e
Source dataset
uspto-grants-2003_12
Patent number
US06670400B1

Reaction notes

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