1,3-Benzodioxole, 5-nitro- → 1,3-Benzodioxol-5-amine

HRID 1973429Notes

Reaction equation

HRID 1973429 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1)([O-])=O.[H][H]>[Pd].C(O)C>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]2[O:10][CH2:11][O:12][C:6]=2[CH:5]=1

Participants

5

Reactant 2

HCID 757981,3-Benzodioxole, 5-nitro-HCID 178418361HCID 178418361, compound

Product 1

HCID 843101,3-Benzodioxol-5-amine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 38 gms. of 1-nitro-3,4-methylenedioxybenzene in 75 mls. of absolute ethanol is added 1.5 gms. of 5% palladium on carbon. The resulting mixture is hydrogenated at approximately 4 atmospheres pressure of hydrogen and ambient temperature for 4 hours. The catalyst is removed by filtration and the filtrate concentrated to a syrup. Trituration of the syrup with petroleum ether (b.p. 30°-60°C.) causes solidification and recrystallization from the same solvent provides 1-amino-3,4-methylenedioxybenzene, m.p. 37°C.

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate concentrated to a syrup
  3. customsolidification and recrystallization from the same solvent

Sources & evidence

ORD record
ord-34abcdb8f41443e1b8576aa93a9c8323
Source dataset
uspto-grants-1976_12
Patent number
US03997564

Reaction notes

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