Sodium Hydroxide → 2-(4-Bromo-2-nitrophenyl)ethan-1-amine

HRID 1793941Notes

Reaction equation

HRID 1793941 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10]C(=O)C(F)(F)F)=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1.[OH-].[Na+]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH2:10])=[C:4]([N+:17]([O-:19])=[O:18])[CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22219483HCID 22219483, compound

Product 1

HCID 222194872-(4-Bromo-2-nitrophenyl)ethan-1-amineYield 98.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4.856 g of N-[2-(4-bromo-2-nitrophenyl)ethyl]-2,2,2-trifluoroacetamide in 56 mL of methanol was added 3.417 mL of 5 mol/L sodium hydroxide solution. After being stirred at room temperature overnight, and at 50° C. overnight, the reaction mixture was concentrated under reduced pressure. To the residue were added ethyl acetate and water, and the mixture was separated. After the aqueous layer was extracted with ethyl acetate, the organic layers were combined, and washed with brine. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure to give 3.44 g of 2-(4-bromo-2-nitrophenyl)ethylamine.

Workup

  1. concentrationat 50° C. overnight, the reaction mixture was concentrated under reduced pressure
  2. additionTo the residue were added ethyl acetate and water
  3. customthe mixture was separated
  4. extractionAfter the aqueous layer was extracted with ethyl acetate
  5. washwashed with brine
  6. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1d651983b4d24b16a8a786fbe1590a8e
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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