(Z)-1-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene → (Z)-1-(3-amino-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene

HRID 2899Notes

Reaction equation

HRID 2899 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:11]=[CH:12]\[C:13]2[CH:18]=[C:17]([O:19][CH3:20])[C:16]([O:21][CH3:22])=[C:15]([O:23][CH3:24])[CH:14]=2)[CH:7]=[CH:8][C:9]=1[CH3:10])([O-])=O>C(O)(=O)C.ClCCl.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:11]=[CH:12]\[C:13]2[CH:14]=[C:15]([O:23][CH3:24])[C:16]([O:21][CH3:22])=[C:17]([O:19][CH3:20])[CH:18]=2)[CH:7]=[CH:8][C:9]=1[CH3:10]

Participants

5

Reactant 1

HCID 10711415(Z)-1-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)ethene

Product 1

HCID 10590264(Z)-1-(3-amino-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl)etheneYield 49.1%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

65 mg of (Z)-1-(3-nitro-4-methylphenyl)-2-(3,4,5-trimethoxyphenyl) ethene were dissolved in 4 ml of acetic acid and 4 ml of dichloromethane, and 300 mg of zinc were added thereto and stirred for one hour. The reaction liquid was filtered, concentrated and purified by silica gel column chromatography (dichloromethane:hexane=2.1 by volume) to obtain 29 mg of the intended compound. The yield was 46.5%.

Workup

  1. customThe reaction liquid
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (dichloromethane:hexane=2.1 by volume)

Sources & evidence

ORD record
ord-8e7d1432c9064f03900f1184067040ee
Source dataset
uspto-grants-1998_03
Patent number
US05731353

Reaction notes

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