Reaktion #70547

ord-ce71b24d047f4be5b9d6e493b0d3be4c

Reaktionsgleichung

COc1ccc(CBr)cc1[N+](=O)[O-]
4-(bromomethyl)-1-methoxy-2-nitrobenzene
CCN(CC)CC
triethylamine
CNCCO
2-(methylamino)ethanol
COc1ccc(CN(C)CCO)cc1[N+](=O)[O-]
title compound
COc1ccc(CN(C)CCO)cc1[N+](=O)[O-]
2-((4-methoxy-3-nitrobenzyl)(methyl)amino)ethanol

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  2. 2
    WaschenThe organic layer was washed with brine
  3. 3
    Trocknendried over Na2SO4
  4. 4
    Filtrationfiltered
  5. 5
    Einengenconcentrated

Vorschrift

A 5 mL round bottom flask was charged with 4-(bromomethyl)-1-methoxy-2-nitrobenzene (0.6 g, 2.44 mmol) and acetonitrile (2 mL). The solution was treated with triethylamine (1 mL, 7.32 mmol) and 2-(methylamino)ethanol (0.585 mL, 7.32 mmol), and the reaction was stirred at ambient temperature for 16 hours. The reaction was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated to provide the title compound. MS (DCI+) m/e 241.1 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536180B2uspto-grants-2013_09