Stannous chloride dihydrate → 3-Aminocinnamic acid ethyl ester

HRID 659094

Reaction equation

HRID 659094 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[CH:7]=[CH:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])([O-])=O.O.O.Cl[Sn]Cl>CCO>[CH2:12]([O:11][C:9](=[O:10])[CH:8]=[CH:7][C:6]1[CH:14]=[CH:15][CH:16]=[C:4]([NH2:1])[CH:5]=1)[CH3:13]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 94827Ethyl-m-nitrocinnamate

Product 1

HCID 978253-Aminocinnamic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl 3-nitrocinnamate (1) (2.0 g, 9.04 mmol) was reduced using method A, except that SnCl2.2H2O (10.2 g, 45.20 mmol) in EtOH (20 mL) was used and after the reaction the solvent was concentrated in vacuo, Rochelle's salt and saturated NaHCO3 (1:1, 80 mL) were added, and the aqueous basified with 1N NaOH. The aqueous was extracted with EtOAc (3×40 mL), washed with Rochelle's salt/saturated NaHCO3 solution (2×40 mL), dried (MgSO4) and the solvent was concentrated in vacuo to give the title compound. Yield: 1.77 g, >100%; LC/MS tr 0.89 min; MS (ES+) m/z 192 (M+H)

Workup

  1. customafter the reaction the solvent
  2. concentrationwas concentrated in vacuo, Rochelle's salt and saturated NaHCO3 (1:1, 80 mL)
  3. additionwere added
  4. extractionThe aqueous was extracted with EtOAc (3×40 mL)
  5. washwashed with Rochelle's salt/saturated NaHCO3 solution (2×40 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-5b0e7255ce0e49e88ae40a507b94bae2
Source dataset
uspto-grants-2011_12
Patent number
US08080567B2

Linked notes

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