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

HRID 1971224Notes

Reaction equation

HRID 1971224 reaction equation
[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]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 30201354-(2-Methoxyethyl)aniline

Product 1

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

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-53cc28f03dd640e5b46a8ad8c7be388d
Source dataset
uspto-grants-2013_04
Patent number
US08431592B2

Reaction notes

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