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

HRID 386436

反応式

HRID 386436 の反応式
[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

参加物

5

反応物 1

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

生成物 1

HCID 417374Methyl 3-(4-aminophenyl)propanoate

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-77a0dd304c9441dd91cb47a29775c16c
出典データセット
uspto-grants-2013_02
特許番号
US08372823B2

関連ノート

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