4-Nitrophenol → 4-(cyclopentyloxy)aniline

HRID 1294830Notes

Reaction equation

HRID 1294830 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-])=O.Br[CH:12]1[CH2:16][CH2:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>O>[CH:12]1([O:10][C:7]2[CH:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:16][CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 9804-NitrophenolHCID 6228DimethylformamideHCID 8728BromocyclopentaneHCID 11430Potassium Carbonate

Product 1

HCID 64844484-(cyclopentyloxy)aniline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4-nitrophenol (63.7 g), bromocyclopentane (68.2 g), potassium carbonate (63.3 g) and DMF (300 mL) was heated at 80° C. for 24 hours. After cooling, it was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over magnesium sulfate and concentrated. The residue was hydrogenated in ethanol using palladium(II) hydroxide as catalyst. The product with the molecular weight of 177.25 (C11H15NO) was obtained in this way; MS (ESI): 178 (M+H+).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe product with the molecular weight of 177.25 (C11H15NO) was obtained in this way

Sources & evidence

ORD record
ord-024e35d98a80490fa18226b209eecce1
Source dataset
uspto-grants-2007_07
Patent number
US07241787B2

Reaction notes

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