Methyl 3-(4-nitrophenyl)-2-propenoate → Methyl 3-(4-aminophenyl)propanoate

HRID 386436

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HRID 386436 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1)([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=1

참가 물질

5

반응물 1

HCID 5354137Methyl 3-(4-nitrophenyl)-2-propenoate

생성물 1

HCID 417374Methyl 3-(4-aminophenyl)propanoate

시약·촉매·용매 3

HCID 23938Palladium촉매HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
25 °C

실험 절차

A solution of methyl (E)-3-(4-nitrophenyl)acrylate (S31, 4.10 g, 19.8 mmol) in MeOH (30 mL) and THF (30 mL) was treated with 10% Pd/C (400 mg). The reaction mixture was purged with H2 and was stirred at 25° C. for 10 h. The suspension was filtered through diatomaceous earth and concentrated to afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid: 1H NMR (CDCl3, 500 MHz) 6.99 (d, 2H, J=8.2 Hz), 6.63 (d, 2H, J=8.4 Hz), 3.60 (s, 3H), 2.85 (t, 2H, J=7.7 Hz), 2.58 (t, 2H, J=7.7 Hz); 13C NMR (CDCl3, 125 MHz) 173.5, 144.6, 130.5, 129.1, 115.3, 51.5, 36.1, 30.1.

후처리

  1. customThe reaction mixture was purged with H2
  2. filtrationThe suspension was filtered through diatomaceous earth
  3. concentrationconcentrated
  4. customto afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid

출처 및 근거

ORD 기록
ord-77a0dd304c9441dd91cb47a29775c16c
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08372823B2

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