Sodium Hydroxide → 1-Chloro-3-(4-aminophenoxy)propane

HRID 1030274Notes

Reaction equation

HRID 1030274 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[CH:8][CH:7]=1.[OH-].[Na+]>CCO>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 118446171-(3-Chloropropoxy)-4-nitrobenzene

Product 1

HCID 198223581-Chloro-3-(4-aminophenoxy)propaneYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1-chloro-3-(4-nitrophenoxy)propane (830 mg, 3.85 mmol), stannous chloride dihydrate (4.3 g, 19.25 mmol), and EtOH (20 mL) was heated under reflux for 3 hours. The mixture was cooled, 2.5N NaOH (19 mL) was added, and the precipitate was removed by filtration. The filtrate was concentrated to 10 mL and extracted with EtOAc. The extracts were dried (MgSO4) and concentrated to give 700 mg (98%) of product as a brown oil.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. temperatureThe mixture was cooled
  4. customthe precipitate was removed by filtration
  5. concentrationThe filtrate was concentrated to 10 mL
  6. extractionextracted with EtOAc
  7. dry with materialThe extracts were dried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a4a9a3e2a9ec4d1cbadba9c6902fe7d1
Source dataset
uspto-grants-1992_04
Patent number
US05104892

Reaction notes

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