2-Methoxyethylamine → (2-Methoxy-ethyl)-(2-methoxy-6-nitro-phenyl)-amine

HRID 1661900Notes

Reaction equation

HRID 1661900 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12].C(N(C(C)C)CC)(C)C.[CH3:22][O:23][CH2:24][CH2:25][NH2:26]>>[CH3:22][O:23][CH2:24][CH2:25][NH:26][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[O:11][CH3:12]

Participants

4

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 124118272-Chloro-1-methoxy-3-nitrobenzene

Product 1

HCID 57772036(2-Methoxy-ethyl)-(2-methoxy-6-nitro-phenyl)-amineYield 85%

Conditions

Temperature
180 °C

Procedure

A mixture of 7.5 g (40 mmol) 2-chloro-1-methoxy-3-nitro-benzene, 14 ml diisopropylethylamine and 35 ml 2-methoxyethyl amine is heated (180° C. oil bath temperature) in a closed steel reactor for 25 min. Then the reaction mixture is cooled to room temperature and is concentrated in vacuo (3× coevaporation with toluene) to obtain ca. 20 g (which contains 85% of the title compound) of a red oil which is used without further purification in the next step.

Workup

  1. temperatureThen the reaction mixture is cooled to room temperature
  2. concentrationis concentrated in vacuo (3× coevaporation with toluene)

Sources & evidence

ORD record
ord-04eab5cce2ca44c6b45ee0f9f8d55aa8
Source dataset
uspto-grants-2011_10
Patent number
US08030497B2

Reaction notes

Loading…