tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate → Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

HRID 626414ノート

反応式

HRID 626414 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][C:3]=1[N+:17]([O-])=O>[Pd].C(OCC)(=O)C>[NH2:17][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][C:2]=1[Cl:1]

参加物

4

反応物 1

HCID 58136394tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

生成物 1

HCID 58136497Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 8857Ethyl Acetate溶媒

実験手順

Under argon, 5.4 g of 10% palladium on carbon were added to a solution of 72.0 g (254 mmol) of tert-butyl (2E)-3-(4-chloro-3-nitrophenyl)acrylate in 1.0 liters of ethyl acetate. The suspension was stirred at RT under a hydrogen atmosphere at standard pressure for 7 h. The reaction mixture was then filtered off with suction through kieselguhr, and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 9:1). This gave 38 g (58% of theory) of the title compound.

後処理

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 9:1)

出典と根拠

ORDレコード
ord-d2f2e41eb4034c2d8e3e95067a9310b4
出典データセット
uspto-grants-2016_04
特許番号
US09309198B2

反応ノート

読み込み中…