Réaction #790927

ord-7509ab5e4b554536b54de0f86dac2bf3

Équation de réaction

O=[N+]([O-])c1ccc2c(c1)OCO2
3,4-methylenedioxynitrobenzene
CC(=O)NCCO
N-acetylethanolamine
CC(=O)NCCOc1ccc([N+](=O)[O-])cc1O
N-(2-hydroxy-4-nitrophenoxyethyl)acetamide

Conditions de réaction

Température
100°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureAfter heating for one hour
  2. 2
    workup.STIRRINGthe reaction medium is stirred at 100° C. for a further 3 hours
  3. 3
    Filtrationis filtered off
  4. 4
    Autreto precipitate the expected product
  5. 5
    FiltrationIt is filtered off
  6. 6
    Lavagewashed with water
  7. 7
    Autredried in vacuo

Mode opératoire

0.05 mol (8.35 g) of 3,4-methylenedioxynitrobenzene is introduced into 42 ml of N-acetylethanolamine. The mixture is heated to the region of 100° C., with stirring, and 0.055 mol (3.7 ml) of 15N potassium hydroxide solution is then added. After heating for one hour, 0.050 mol (3.3 ml) of 15N potassium hydroxide solution is added and the reaction medium is stirred at 100° C. for a further 3 hours and then poured onto 120 g of crushed ice. The unreacted starting material, which is insoluble in an alkaline medium, is filtered off. The filtrate is then acidified to pH=5.6 with hydrochloric acid in order to precipitate the expected product. It is filtered off, washed with water and dried in vacuo. It melts at 165° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US04985042uspto-grants-1991_01