Triphenylphosphine → 1-(3-Nitrophenyl)ethanamine

HRID 840591Notes

Reaction equation

HRID 840591 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]([N:12]=[N+]=[N-])[CH3:11])[CH:5]=1)([O-:3])=[O:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[CH:10]([NH2:12])[CH3:11])([O-:3])=[O:2]

Participants

6

Reactant 3

HCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 183758741-(1-Azidoethyl)-3-nitrobenzene

Product 1

HCID 5919961-(3-Nitrophenyl)ethanamineYield 97.9%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Nitro-3-(1-azidoethyl)benzene (1.3 g, 6.76 mmol) was dissolved in tetrahydrofuran and triphenylphosphine (1.9 g, 7.4 mmol) was added. The resulting solution was stirred at ambient temperature for 18 hours. 1M aqueous sodium hydroxide (1 ml) was then added and the stirring continued for 48 hours. The reaction was diluted with ethyl acetate, washed with brine several times, dried over magnesium sulfate, filtered, and evaporated. The residue was chromatographed (silica gel, 2:1 hexane:ethyl acetate) to provide 1.1 g of the title compound. (99%). 1H NMR(CDCl3)

Workup

  1. waitthe stirring continued for 48 hours
  2. washwashed with brine several times
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed (silica gel, 2:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-565e863cca2f49358b9c252b2163b04e
Source dataset
uspto-grants-2002_04
Patent number
US06369070B1

Reaction notes

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