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

HRID 2906Notes

Reaction equation

HRID 2906 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[Cl: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: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[Cl:10]

Participants

4

Reactant 1

HCID 10619446(E)-3-(3-nitro-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile

Product 1

HCID 11791765(E)-3-(3-amino-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrileYield 33.6%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

(E)-3-(3-nitro-4-chlorophenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile 330 mg was dissolved in 8 ml of acetic acid then zinc was added to the mixture. The mixture was stirred vigorously for one hour then filtered and concentrated. The residue was purified on a silica gel plate (dichloromethane) to give 102 mg of desired product (yield 33%).

Workup

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

Sources & evidence

ORD record
ord-7addc825e2ab4603a52563957c8959bb
Source dataset
uspto-grants-1998_03
Patent number
US05731353

Reaction notes

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