methyl(2E)-3-(4-methoxy-2-nitrophenyl)acrylate → HCID 23003572, compound

HRID 1644282Notes

Reaction equation

HRID 1644282 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12])=[C:5]([N+:15]([O-])=O)[CH:4]=1>C(O)(=O)C.[Zn]>[NH2:15][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1/[CH:9]=[CH:10]/[C:11]([O:13][CH3:14])=[O:12]

Participants

4

Reactant 1

HCID 11791213methyl(2E)-3-(4-methoxy-2-nitrophenyl)acrylate2×

Product 1

HCID 23003572HCID 23003572, compoundYield 23.4%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl(2E)-3-(4-methoxy-2-nitrophenyl)acrylate (Intermediate 5, 4.9 g, 20.66 mmol) in acetic acid (150 mL) at room temperature under nitrogen was added zinc powder (7.7 g, 118 mmol) in portions. After 4 hours, another 5 g of zinc was added and the resulting reaction mixture was heated at 50° C. for two hours. The reaction mixture was then cooled to room temperature, filtered, and the filtrate was concentrated to dryness under reduced pressure. The residue was chromatographed on silica gel with hexanes/ethyl acetate (3:1) to give 1.0 g (23% yield) of product as a yellow solid, mp 149° C.

Workup

  1. customthe resulting reaction mixture
  2. temperatureThe reaction mixture was then cooled to room temperature
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated to dryness under reduced pressure
  5. customThe residue was chromatographed on silica gel with hexanes/ethyl acetate (3:1)

Sources & evidence

ORD record
ord-d246abde0d0d4b238d897480c338c841
Source dataset
uspto-grants-2012_02
Patent number
US08124602B2

Reaction notes

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