Hydrochloric Acid → 3-(Cyclopentyloxy)-4-methoxyaniline

HRID 2230998Notes

Reaction equation

HRID 2230998 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([N+:15]([O-])=O)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[NH2:15])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 113907411-Cyclopentyloxy-2-methoxy-5-nitrobenzene

Product 1

HCID 27793343-(Cyclopentyloxy)-4-methoxyanilineYield 59.3%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of 3-cyclopentyloxy-4-methoxy-1-nitrobenzene (5.02 g), iron powder (4.8 g) and hydrochloric acid (35%, 15 ml) in ethanol (40 ml) was stirred under reflux for 3 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated to give 3-cyclopentyloxy-4-methoxyaniline (2.60 g) as an oil.

Workup

  1. temperatureunder reflux for 3 hours
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6794631496a742dc91ed50d76b466602
Source dataset
uspto-grants-2002_07
Patent number
US06426345B1

Reaction notes

Loading…