(E)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile → (E)-3-(3-amino-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile

HRID 260101Notes

Reaction equation

HRID 260101 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:11]=[C:12](\[C:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18]([O:23][CH3:24])=[C:17]([O:25][CH3:26])[CH:16]=2)/[C:13]#[N:14])[CH:7]=[CH:8][C:9]=1[CH3:10])([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:11]=[C:12](\[C:15]2[CH:16]=[C:17]([O:25][CH3:26])[C:18]([O:23][CH3:24])=[C:19]([O:21][CH3:22])[CH:20]=2)/[C:13]#[N:14])[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

4

Reactant 1

HCID 10522056(E)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile

Product 1

HCID 10853426(E)-3-(3-amino-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrileYield 78%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

84 mg of (E)-3-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile was dissolved in 8 ml of acetic acid then zinc was added to the mixture. The mixture was stirred vigorously for 1 hour then filtered and concentrated. The residue was purified on a silica gel plate (dichloromethane) to give 60 mg of the intended compound.

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated
  3. customThe residue was purified on a silica gel plate (dichloromethane)

Sources & evidence

ORD record
ord-c9362c38d3fe42b792200108ae178a8e
Source dataset
uspto-grants-1996_06
Patent number
US05525632

Reaction notes

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