4-Nitrophenol → 4-(cyclopentyloxy)aniline

HRID 2426608Notes

Reaction equation

HRID 2426608 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 by method B. This resulted in the product with the molecular weight of 177.25 (C11H15NO); 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. customThis resulted in the product with the molecular weight of 177.25 (C11H15NO)

Sources & evidence

ORD record
ord-dcf5bb4a1d6e491cb3f246ba91a88178
Source dataset
uspto-grants-2011_06
Patent number
US07968550B2

Reaction notes

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