Nitric Acid → 2-(5-Methoxy-2-nitrophenyl)ethan-1-amine

HRID 1861960Notes

Reaction equation

HRID 1861960 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][NH2:11])[CH:6]=[CH:7][CH:8]=1.O.[OH-].[Na+].[N+:15]([O-])([OH:17])=[O:16]>C(Cl)(Cl)Cl.S(=O)(=O)(O)O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:15]([O-:17])=[O:16])=[C:5]([CH2:9][CH2:10][NH2:11])[CH:4]=1

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 748663-Methoxyphenethylamine

Product 1

HCID 186219752-(5-Methoxy-2-nitrophenyl)ethan-1-amineYield 21%

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidSolventHCID 6212ChloroformSolvent

Procedure

To a solution of 2-(3-methoxyphenyl)ethylamine (1.51 g) in chloroform (30 ml), fuming nitric acid (specific gravity=1.52; 0.84 ml) and sulfuric acid (1.07 ml) were successively added dropwise under ice cooling and stirred under ice cooling for 3 h. Water and 2 N aqueous sodium hydroxide solution were added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=9:1) to give 400 mg of the titled compound (yield, 21%)

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (eluent, chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-c0f0c8b298bd4fbc9552e68017395bf8
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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