2-Methoxyethanol → 4-(beta-Methoxyethoxy)-2-(beta-hydroxyethyl)amino-6-(beta-hydroxyethyl)aminonitrobenzene

HRID 1606860Notes

Reaction equation

HRID 1606860 reaction equation
Cl[C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([N+:12]([O-:14])=[O:13])=[C:4]([NH:15][CH2:16][CH2:17][OH:18])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:25][O:26][CH2:27][CH2:28][OH:29]>CN1CCCC1=O>[CH3:25][O:26][CH2:27][CH2:28][O:29][C:2]1[CH:7]=[C:6]([NH:8][CH2:9][CH2:10][OH:11])[C:5]([N+:12]([O-:14])=[O:13])=[C:4]([NH:15][CH2:16][CH2:17][OH:18])[CH:3]=1

Participants

5

Reactant 3

HCID 80192-MethoxyethanolHCID 11430Potassium CarbonateHCID 200710912-(beta-Hydroxyethyl)amino-6-(beta-hydroxyethyl)amino-4-chloronitrobenzene

Product 1

HCID 198511744-(beta-Methoxyethoxy)-2-(beta-hydroxyethyl)amino-6-(beta-hydroxyethyl)aminonitrobenzene

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.09 mole (25 g) of 4-chloro-2-(β-hydroxyethyl)amino-6-(β-hydroxyethyl)aminonitrobenzene, synthesized in stage 1 of example 2, was added to a solution of 11.9 g of pelletized potash in 60 ml of 2-methoxyethanol and 25 ml of N-methylpyrrolidone and heated for 4 hours over a boiling water bath. The reaction medium was diluted with 350 ml of ice water and the desired product obtained by high pressure liquid chromatography (HPLC). About 150 ml of the aqueous solution obtained by dilution of the reaction medium were injected onto a C18RD chromatographic column (Instrument: Waters Prep 500). The desired product was eluted by a 40% methanol--60% water solution. After evaporation of the fractions containing the desired product, a dry extract was obtained which was recrystallized from isopropanol. After recrystallization, it melted at 116° C.

Workup

  1. temperatureheated for 4 hours over a boiling water bath

Sources & evidence

ORD record
ord-924f1e9b6d5943628af752863d032451
Source dataset
uspto-grants-1989_09
Patent number
US04863482

Reaction notes

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