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

HRID 890771Notes

Reaction equation

HRID 890771 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) δ 6.95 (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-59665a9d654b48b59c21a81adeebe281
Source dataset
uspto-grants-2006_02
Patent number
US06998423B2

Reaction notes

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