Hydrazine → 2-(4-Fluorophenoxy)ethanamine

HRID 1895923Notes

Reaction equation

HRID 1895923 reaction equation
NN.[F:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][N:11]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:6][CH:5]=1>CO>[F:3][C:4]1[CH:23]=[CH:22][C:7]([O:8][CH2:9][CH2:10][NH2:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 9321HydrazineHCID 22303522-[2-(4-Fluorophenoxy)ethyl]isoindole-1,3-dione

Product 1

HCID 31358492-(4-Fluorophenoxy)ethanamineYield 72.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Hydrazine solution (138 mg, 2.75 mmol) was added to a solution of 2-(2-(4-fluorophenoxy)ethyl)isoindoline-1,3-dione (713 mg, 2.5 mmol) in methanol (8 ml) and stirred at room temperature for 4 hours. The resulting solid was filtered off and concentrated in vacuo. The residue was triturated with diethyl ether (30 ml), and the resulting solid was filtered off again and concentrated in vacuo to give 2-(4-fluorophenoxy)ethanamine (280 mg, 70%) as colorless oil: LCMS: 325 [M+1]+.

Workup

  1. filtrationThe resulting solid was filtered off
  2. concentrationconcentrated in vacuo
  3. customThe residue was triturated with diethyl ether (30 ml)
  4. filtrationthe resulting solid was filtered off again
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6c197e61345f4cb794e6c7fd6a4fff23
Source dataset
uspto-grants-2013_08
Patent number
US08518934B2

Reaction notes

Loading…