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

HRID 2086822Notes

Reaction equation

HRID 2086822 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-b92a2477eb5c457a82b95eb10bd296f6
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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