Acetic Acid → HCID 58056098, compound

HRID 1773518Notes

Reaction equation

HRID 1773518 reaction equation
[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([N+:14]([O-])=O)[CH:7]=1.C(O)(=O)C>ClCCl.[Zn]>[CH3:1][O:2][C:3](=[O:17])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([NH2:14])[CH:7]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 46243463HCID 46243463, compound

Product 1

HCID 58056098HCID 58056098, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (E)-3-(4-methoxy-3-nitro-phenyl)-acrylic acid methyl ester (0.5 g) in dichloromethane (5 mL) was added zinc dust (2 g), followed by acetic acid (1 mL) and the resulting mixture was stirred at room temperature for 30 minutes. The solid was filtered off and washed with dichloromethane. The filtrate was evaporated under reduced pressure and the residue was purified by flash chromatography (DCM/acetone, 95/5) to give (E)-3-(3-amino-4-methoxy-phenyl)-acrylic acid methyl ester.

Workup

  1. filtrationThe solid was filtered off
  2. washwashed with dichloromethane
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe residue was purified by flash chromatography (DCM/acetone, 95/5)

Sources & evidence

ORD record
ord-e49518fac75f438b84f9bef9b168d312
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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