1,3-Benzodioxole, 5-nitro- → HCID 53695531, compound

HRID 703746Notes

Reaction equation

HRID 703746 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=2[O:2]1.[CH3:13][N:14]([C:18](=[O:20])[CH3:19])[CH2:15]CO>>[CH3:13][N:14]([CH2:15][CH2:1][O:9][C:8]1[CH:7]=[CH:6][C:5]([N+:10]([O-:12])=[O:11])=[CH:4][C:3]=1[OH:2])[C:18](=[O:20])[CH3:19]

Participants

3

Reactant 2

HCID 757981,3-Benzodioxole, 5-nitro-HCID 10510843N-(2-hydroxyethyl)-N-methylacetamide

Product 1

HCID 53695531HCID 53695531, compound

Conditions

Temperature
100 °C

Procedure

0.1 mol (16.7 g) of 3,4-methylenedioxynitrobenzene is introduced into 67 ml of N-methyl-N-acetylethanolamine. The mixture is heated to the region of 100° C., with stirring, and 11 ml of 15N potassium hydroxide solution are then added. After stirring for 4 hours at 100° C., the reaction medium is poured onto 200 g of crushed ice. The unreacted starting material, which is insoluble in an alkaline medium, is removed by filtration. The filtrate is then brought to a pH of 5 with hydrochloric acid. The expected nitro product which has precipitated is filtered off. After washing with water, drying and recrystallization from a 50/50 ethyl acetate/ethanol mixture, the product melts at 158° C.

Workup

  1. stirringAfter stirring for 4 hours at 100° C.
  2. customis removed by filtration
  3. customThe expected nitro product which has precipitated
  4. filtrationis filtered off
  5. washAfter washing with water
  6. customdrying
  7. customrecrystallization from a 50/50 ethyl acetate/ethanol mixture

Sources & evidence

ORD record
ord-c8ec3a2cb9a04b128d0fcb1e8421f82a
Source dataset
uspto-grants-1991_01
Patent number
US04985042

Reaction notes

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