Diethyl Ether → 2-(3,5-Dichlorophenoxy)ethylamine

HRID 1699036Notes

Reaction equation

HRID 1699036 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[O:5][CH2:6][CH2:7][N:8]1C(=O)C2C(=CC=CC=2)C1=O.O.NN.CCOCC.[OH-].[K+]>CO>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[C:20]([Cl:22])[CH:21]=1)[O:5][CH2:6][CH2:7][NH2:8]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 7571580HCID 7571580, compound

Product 1

HCID 499912-(3,5-Dichlorophenoxy)ethylamineYield 109.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-[2-(3,5-dichloro-phenoxy)-ethyl]-isoindole-1,3-dione (1.29 g, 3.84 mmol) and hydrazine hydrate (202 mg, 4.05 mmol) in MeOH (16 mL) was heated at reflux for 2 h. The mixture was cooled to room temperature and Et2O was added. The suspension was shaken with 40% aqueous potassium hydroxide. The aqueous solution was extracted with Et2O (3×) and the combined organic layers were dried (K2CO3), filtered, and concentrated to provide the title compound (870 mg). 1HNMR (400 MHz, CDCl3) δ6.95 (m, 1H), 6.80 (m, 2H), 3.95 (m, 2H), 3.07 (t, 2H), 1.70 (bs, 2H).

Workup

  1. temperatureat reflux for 2 h
  2. extractionThe aqueous solution was extracted with Et2O (3×)
  3. dry with materialthe combined organic layers were dried (K2CO3)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7f3cda68e6244781ab1835d4f3fef47b
Source dataset
uspto-grants-2002_02
Patent number
US06344485B1

Reaction notes

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