Chlorosuccinimide → 2-Chloro-4-(2-methoxy-ethyl)-phenylamine

HRID 1446115ノート

反応式

HRID 1446115 の反応式
[CH3:1][O:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[CH:7][CH:6]=1.[Cl:12]N1C(=O)CCC1=O>C(O)(C)C>[Cl:12][C:7]1[CH:6]=[C:5]([CH2:4][CH2:3][O:2][CH3:1])[CH:10]=[CH:9][C:8]=1[NH2:11]

参加物

4

反応物 2

HCID 31398ChlorosuccinimideHCID 30201354-(2-Methoxyethyl)aniline

生成物 1

HCID 536303492-Chloro-4-(2-methoxy-ethyl)-phenylamine

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒

実験手順

2 g (13.2 mmol) of 4-(2-methoxy-ethyl)-phenylamine (Example 42b) and 1.85 g (13.9 mmol) of N-chlorosuccinimide (Aldrich, Buchs, Switzerland) in 26 ml of isopropanol are stirred at rt for 30 min. The reaction mixture is evaporated to dryness and the residue is taken in EtOAc. The organic layers is washed with sat. aqueous NaHCO3 (2×), dried over MgSO4, filtered and evaporated. The residue is purified by flash chromatography on silica gel (hexane-EtOAc 5:1 to 2:1) to provide the title compound as an oil. ES-MS: 186 (M+H)+; analytical HPLC: tret=2.42 minutes (Grad 1).

後処理

  1. customThe reaction mixture is evaporated to dryness
  2. washThe organic layers is washed with sat. aqueous NaHCO3 (2×)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue is purified by flash chromatography on silica gel (hexane-EtOAc 5:1 to 2:1)

出典と根拠

ORDレコード
ord-adb554ea4fd04a65b306faafa3e8214b
出典データセット
uspto-grants-2010_02
特許番号
US07667039B2

反応ノート

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