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

HRID 2901Notes

Reaction equation

HRID 2901 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:12]=[C:13](\[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=2)/[C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11])([O-])=O>C(O)(=O)C.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:12]=[C:13](\[C:16]2[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=2)/[C:14]#[N:15])[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 1

HCID 10666833(E)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile

Product 1

HCID 9840884(E)-3-(3-amino-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-enenitrileYield 99.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

500 mg of (E)-3-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl)-prop-2-ene-nitrile were dissolved in 25 ml of acetic acid, and 5 g of zinc were added thereto and stirred for 30 minutes at room temperature. The reaction liquid was filtered and then concentrated. The concentrated liquid was purified by silica gel column chromatography (ethyl acetate:hexane--1.2 by volume) to obtain 457 mg of the intended compound. The yield was 99%.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. customThe concentrated liquid was purified by silica gel column chromatography (ethyl acetate:hexane--1.2 by volume)

Sources & evidence

ORD record
ord-ed51f9672c6c4e2fa5a22df5f59b9419
Source dataset
uspto-grants-1998_03
Patent number
US05731353

Reaction notes

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