(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 260098Notes

Reaction equation

HRID 260098 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-623c33618a484101a7535c84b2588b02
Source dataset
uspto-grants-1996_06
Patent number
US05525632

Reaction notes

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