(Z)-1,2,3-trimethoxy-5-(4-methoxy-3-nitrostyryl)benzene → AC-7739 free base

HRID 2896Notes

Reaction equation

HRID 2896 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:12]=[CH:13]\[C:14]2[CH:19]=[C:18]([O:20][CH3:21])[C:17]([O:22][CH3:23])=[C:16]([O:24][CH3:25])[CH:15]=2)[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]=[CH:13]\[C:14]2[CH:15]=[C:16]([O:24][CH3:25])[C:17]([O:22][CH3:23])=[C:18]([O:20][CH3:21])[CH:19]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH3:11]

Participants

4

Reactant 1

HCID 10617491(Z)-1,2,3-trimethoxy-5-(4-methoxy-3-nitrostyryl)benzene

Product 1

HCID 9796936AC-7739 free baseYield 49.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

700 mg of (Z)-1-(3-nitro-4-methoxyphenyl)-2-(3,4,5-trimethoxyphenyl) ethene were dissolved in 35 ml of acetic acid, and 7 g 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 314 mg of the intended compound. The yield was 49.3%.

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-aa0f7fe1f9b24e3d99fc0030bef32d89
Source dataset
uspto-grants-1998_03
Patent number
US05731353

Reaction notes

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