Stannous chloride dihydrate → 3-Aminocinnamic acid ethyl ester

HRID 659094

반응식

HRID 659094 반응식
[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]

참가 물질

4

반응물 2

HCID 61436Stannous chloride dihydrateHCID 94827Ethyl-m-nitrocinnamate

생성물 1

HCID 978253-Aminocinnamic acid ethyl ester

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)

후처리

  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

출처 및 근거

ORD 기록
ord-5b0e7255ce0e49e88ae40a507b94bae2
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080567B2

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