Sodium Hydroxide → 2-(5-Fluoro-2-methoxyphenyl)ethan-1-amine

HRID 2110247Notes

Reaction equation

HRID 2110247 reaction equation
[Cl-].[Cl-].[Cl-].[Al+3].[H-].[Al+3].[Li+].[H-].[H-].[H-].[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH2:18][C:19]#[N:20])[CH:17]=1.[OH-].[Na+]>C1COCC1>[F:11][C:12]1[CH:13]=[CH:14][C:15]([O:21][CH3:22])=[C:16]([CH2:18][CH2:19][NH2:20])[CH:17]=1

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 3026852-(5-Fluoro-2-methoxyphenyl)acetonitrileHCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydride

Product 1

HCID 220150102-(5-Fluoro-2-methoxyphenyl)ethan-1-amine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Under argon, 17.6 g (132 mmol) of aluminium trichloride are dissolved in THF, and the mixture is cooled to 0° C. 87 ml of lithium aluminium hydride solution (1M in THF) are slowly added dropwise. A solution of 14.5 g (87.8 mmol) of (5-fluoro-2-methoxyphenyl)acetonitrile in 100 ml is added slowly. The reaction mixture is stirred at RT for 2 hours. At 0° C., ice/water is then added, the mixture is made alkaline using sodium hydroxide solution and extracted with ethyl acetate and the extract is dried and concentrated using a rotary evaporator.

Workup

  1. extractionextracted with ethyl acetate
  2. customthe extract is dried
  3. concentrationconcentrated
  4. customa rotary evaporator

Sources & evidence

ORD record
ord-6360fed7d50b40e38d4c606c6fad9775
Source dataset
uspto-grants-2009_04
Patent number
US07517896B2

Reaction notes

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