Water → 4-(2-Aminoethyl)-3-fluoroaniline

HRID 1861941Notes

Reaction equation

HRID 1861941 reaction equation
[H-].[Li+].[Al+3].[H-].[H-].[H-].[C:7]([CH2:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[F:17])#[N:8].O.[OH-].[Na+]>C(OCC)C.S(=O)(=O)(O)O>[NH2:8][CH2:7][CH2:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][C:11]=1[F:17]

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18621981(4-Amino-2-fluorophenyl)acetonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 186219114-(2-Aminoethyl)-3-fluoroanilineYield 107.1%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 3283Diethyl EtherSolvent2×

Procedure

To a suspension of aluminum lithium hydride (76 mg) in diethyl ether (5 ml), conc. sulfuric acid (0.053 ml) was added under ice cooling and stirred at room temperature for 1 h. Subsequently, a solution of the compound (100 mg) obtained in Example 251 in diethyl ether (15 ml) was added dropwise at room temperature and heated under reflux for 18 h. To the reaction mixture, water (1 ml) and 2 N aqueous sodium hydroxide solution (10 ml) were added under ice cooling and the mixture was extracted with diethyl ether; the organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure to give 110 mg of the titled compound quantitatively.

Workup

  1. additionwas added under ice cooling
  2. temperatureheated
  3. temperatureunder reflux for 18 h
  4. extractionthe mixture was extracted with diethyl ether
  5. dry with materialthe organic layer was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-0a31c2f536eb4f8190c0ad652209d765
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

Loading…