(2Z)-2-(3,4-dimethoxyphenyl)-3-[5-(3-nitrophenyl)furan-2-yl]prop-2-enenitrile → (Z)-3-[5-(3-amino-phenyl)-furan-2-yl]-2-(3,4-dimethoxy-phenyl)-acrylonitrile

HRID 2366377Notes

Reaction equation

HRID 2366377 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5](/[C:11](=[CH:14]/[C:15]2[O:16][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([N+:26]([O-])=O)[CH:21]=3)=[CH:18][CH:19]=2)/[C:12]#[N:13])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]>[Zn].C(O)(=O)C>[NH2:26][C:22]1[CH:21]=[C:20]([C:17]2[O:16][C:15](/[CH:14]=[C:11](/[C:5]3[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)\[C:12]#[N:13])=[CH:19][CH:18]=2)[CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 1

HCID 1179011(2Z)-2-(3,4-dimethoxyphenyl)-3-[5-(3-nitrophenyl)furan-2-yl]prop-2-enenitrile

Product 1

HCID 11842656(Z)-3-[5-(3-amino-phenyl)-furan-2-yl]-2-(3,4-dimethoxy-phenyl)-acrylonitrileYield 24%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Acetic acid (300 mL) was added to Compound 21 (1.00 g) to form suspension. Zinc powder (3.47 g) was added to the suspension, followed by stirring at room temperature for 4 hours. The reaction mixture was subjected to filtration by use of a celite pad, and the celite pad was washed with chloroform. The filtrate (acetic acid-chloroform solution) was evaporated to dryness. The residue was purified by silica gel column chromatography (chloroform-methanol), to thereby yield the target product (yield: 184 mg, 24%).

Workup

  1. customto form suspension
  2. filtrationThe reaction mixture was subjected to filtration by use of a celite pad
  3. washthe celite pad was washed with chloroform
  4. customThe filtrate (acetic acid-chloroform solution) was evaporated to dryness
  5. customThe residue was purified by silica gel column chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-e86a1f3ff1764e9896384f442eb72baa
Source dataset
uspto-grants-2014_04
Patent number
US08697742B2

Reaction notes

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