5,6-Dinitro-1,3-benzodioxole → 6-Nitro-1,3-benzodioxol-5-amine

HRID 577612

Reaction equation

HRID 577612 reaction equation
[N+:1]([C:4]1[C:12]([N+:13]([O-])=O)=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]>C(O)(=O)C>[N+:1]([C:4]1[C:12]([NH2:13])=[CH:11][C:7]2[O:8][CH2:9][O:10][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

3

Reactant 1

HCID 6113255,6-Dinitro-1,3-benzodioxole

Product 1

HCID 6026656-Nitro-1,3-benzodioxol-5-amineYield 84.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Compound 5,6-dinitrobenzo[d][1,3]dioxole (6.0 g, 28.3 mmol) was added to stirred glacial acetic acid (120 mL) under N2 atmosphere. After the mixture was heated to boiling, the heat source was removed and iron powder (4.75 g) added with vigorous stirring. Quick spontaneous boiling occurred, the mixture turned dark and the exothermic reaction subsided (2-5 min). The mixture was refluxed for 10 min and poured into ice/water. The orange-red product was isolated by filtration, dissolved in glacial acetic acid, and the solution filtered while hot. The filtrate was poured into ice-cold water. The orange-red solid product was isolated by filtration and dried to provide compound 6-nitrobenzo[d][1,3]dioxol-5-amine (4.35 g, 84%). LCMS: 183 [M+1]+; 1H NMR (DMSO-d6) δ 6.06 (s, 2H), 6.51 (s, 1H), 7.36 (s, 1H), 7.73 (s, 2H).

Workup

  1. temperatureAfter the mixture was heated
  2. customthe heat source was removed
  3. additioniron powder (4.75 g) added with vigorous stirring
  4. customthe exothermic reaction
  5. custom(2-5 min)
  6. temperatureThe mixture was refluxed for 10 min
  7. customThe orange-red product was isolated by filtration
  8. filtrationthe solution filtered while hot
  9. additionThe filtrate was poured into ice-cold water
  10. customThe orange-red solid product was isolated by filtration
  11. customdried

Sources & evidence

ORD record
ord-6e6029a8c7c24decb7ed0e385748c29e
Source dataset
uspto-grants-2015_05
Patent number
US09040556B2

Linked notes

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