Phenol → HCID 59442723, compound

HRID 388246Notes

Reaction equation

HRID 388246 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].[CH:18](I)([CH3:20])[CH3:19].[C:22]1(O)[CH:27]=CC=C[CH:23]=1.C1(O)C=CC=CC=1.NC1C=CC=CC=1>CN(C)C=O.C(OCC)(=O)C.O>[CH:18]([O:11][C:3]1[CH:4]=[CH:5][C:6]([N+:8]([O-:10])=[O:9])=[CH:7][C:2]=1[NH:1][CH:22]([CH3:27])[CH3:23])([CH3:20])[CH3:19]

Participants

9

Reactant 5

HCID 996PhenolHCID 6362Isopropyl iodideHCID 11430Potassium CarbonateHCID 36133892-Amino-4-NitrophenolHCID 19829566HCID 19829566, compound

Product 1

HCID 59442723HCID 59442723, compoundYield 10%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-amino-4-nitrophenol 28 (15 g, 97.32 mmol, 1 equiv) in dimethylformamide (300 mL) under nitrogen gas, was added potassium carbonate (40.35 g, 292 mmol, 3 equiv) and isopropyl iodide (9.73 mL, 16.54 g, 97.32 mmol, 1 equiv), then the reaction mixture was stirred at ambient temperature overnight. LCMS analysis of the reaction mixture indicated a mixture of starting material:phenol alkylation: aniline phenol dialkylation (20:13:67). The reaction mixture was diluted with ethyl acetate and water. The layers were separated, and the organic layer was washed with water 1×, dried over Na2SO4, filtered, and concentrated. The crude reaction mixture was purified by flash chromatography and eluted with dichloromethane to provide 2-isopropoxy-N-isopropyl-5-nitrobenzenamine 29 (2.42 g, 10%) as an oil.

Workup

  1. additiona mixture of starting material
  2. customThe layers were separated
  3. washthe organic layer was washed with water 1×
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude reaction mixture
  8. customwas purified by flash chromatography
  9. washeluted with dichloromethane

Sources & evidence

ORD record
ord-bfb2d3df7c5346eb88f11c3159d7e9de
Source dataset
uspto-grants-2013_02
Patent number
US08377924B2

Reaction notes

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