Hydrochloric Acid → (E)-Stilbene-3-amine

HRID 2086774Notes

Reaction equation

HRID 2086774 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 9775603-Nitro-trans-stilbene

Product 1

HCID 5375423(E)-Stilbene-3-amineYield 65.1%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

A mixture of (E)-3-nitrostilbene (3.63 g), hydrochloric acid (35%, 10 ml) and iron powder (3.6 g) in ethanol (30 ml) was refluxed for 1 hour. The mixture was poured into aqueous sodium bicarbonate solution and extracted with ethyl acetate twice. The combined organic solution was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give (E)-3-aminostilbene (2.05 g).

Workup

  1. temperaturewas refluxed for 1 hour
  2. extractionextracted with ethyl acetate twice
  3. washThe combined organic solution was washed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe resultant solid was collected
  7. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-0a0c9850cac3440aa59c2c551dd02299
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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