Methyl 3-(2-nitrophenyl)prop-2-enoate → Methyl 2-aminocinnamate

HRID 1919553Notes

Reaction equation

HRID 1919553 reaction equation
[N+:1]([C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9])([O-])=O.Cl[Sn]Cl.O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:1][C:4]1[CH:15]=[CH:14][CH:13]=[CH:12][C:5]=1[CH:6]=[CH:7][C:8]([O:10][CH3:11])=[O:9]

Participants

5

Reactant 3

HCID 220809Methyl 3-(2-nitrophenyl)prop-2-enoateHCID 516892Sodium BicarbonateHCID 43835034Tin dichloride dihydrate

Product 1

HCID 53439609Methyl 2-aminocinnamateYield 90.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 2-nitrocinnamate (8) (11.03 g, 53.24 mmol) in ethyl acetate (200 ml) was added SnCl2.H2O (60.06 g, 266.19 mmol) at room temperature, and the resulting solution was stirred at 70° C. for 60 minutes. After the reaction was completed, the solution was allowed to cool to room temperature, basified with a saturated aqueous solution of sodium bicarbonate to weak basicity, and filtered with celite. The aqueous phase was extracted with ethyl acetate three times, and the combined organic phase was dried with anhydrous magnesium sulfate and distilled under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent: ethyl acetate:hexane=1:5) to give the target compound (8.50 g, 90%).

Workup

  1. temperatureto cool to room temperature
  2. filtrationfiltered with celite
  3. extractionThe aqueous phase was extracted with ethyl acetate three times
  4. dry with materialthe combined organic phase was dried with anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-c952aeb9b48f4580a35321df13a1dbe6
Source dataset
uspto-grants-2012_05
Patent number
US08168646B2

Reaction notes

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