Hydrazine hydrate (1:1) → 5-Nitroso-1,3-benzodioxole

HRID 327491

Reaction equation

HRID 327491 reaction equation
[CH2:1]1[O:12][C:4]2[CH:5]=[C:6]([N+:9]([O-])=[O:10])[CH:7]=[CH:8][C:3]=2[O:2]1.O.NN>O1CCCC1.[Rh].O.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[CH2:1]1[O:12][C:4]2[CH:5]=[C:6]([N:9]=[O:10])[CH:7]=[CH:8][C:3]=2[O:2]1

Participants

7

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 757981,3-Benzodioxole, 5-nitro-

Product 1

HCID 190017645-Nitroso-1,3-benzodioxole

Reagents, catalysts & solvents 4

HCID 23948RhodiumCatalystHCID 16211236Trichloroiron;hexahydrateCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

1,2-Methylenedioxy-4-nitrobenzene (8.3 g, 0.05 mol) was dissolved in tetrahydrofuran (150 ml) with rhodium on carbon catalyst (0.2 g) at 0° C. and was treated dropwise with hydrazine hydrate (2.8 g, 0.055 mol). On completion of the addition, the mixture was stirred for 1 hour and then filtered through a HYFLO (Trade Mark) filter. The resulting solution was added dropwise to a chilled, stirred solution of iron (III) chloride hexahydrate (27.5 g, 0.1 mol) in water (150 ml). On completion of the addition, water (220 ml) was added and the green precipitate was filtered off, washed with water and dried overnight under high vacuum. 1,2-Methylenedioxy-4-nitrosobenzene was obtained as a green solid (3.7 g, 50% yield) by column chromatography eluting on silica with dichloromethane. M.p. 90°-92° C. M+ (CI):152 (M+ +H)

Workup

  1. additionOn completion of the addition
  2. filtrationfiltered through a HYFLO (Trade Mark)
  3. filtrationfilter
  4. additionThe resulting solution was added dropwise to a chilled
  5. additionwas added
  6. filtrationthe green precipitate was filtered off
  7. washwashed with water
  8. customdried overnight under high vacuum

Sources & evidence

ORD record
ord-e744e40c780d48928fee323323d0615a
Source dataset
uspto-grants-1993_12
Patent number
US05273997

Linked notes

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