Acetic Acid → 6-Nitro-1,3-benzodioxol-5-amine

HRID 1583778Notes

Reaction equation

HRID 1583778 reaction equation
[NH:1]([C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)C(C)=O.C[O-].[Na+].C(O)(=O)C>CO>[NH2:1][C:5]1[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 540215N-(6-Nitro-1,3-benzodioxol-5-yl)acetamideHCID 10942334Sodium Methoxide

Product 1

HCID 6026656-Nitro-1,3-benzodioxol-5-amineYield 95.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

40 g of 5-acetamino-6-nitro-1,3-benzodioxole were dissolved with heating in 4 l of methanol in a 10 l round flask equipped with a reflux condenser. To this hot solution was added a boiling solution of 40 g of sodium methoxide in 4 l of methanol and the mixture was boiled under reflux for exactly 15 minutes. Then, the reaction was interrupted by adding 220 ml of glacial acetic acid. The methanol was removed by distillation and the last traces thereof, together with the glacial acetic acid, were removed by a two-fold evaporation with toluene. The product went into solution with 3 l of methylene chloride and could be freed from the organic residues by suction filtration. The methylene chloride solution was filtered through silicon dioxide and evaporated in vacuo. The residue, recrystallized from isopropanol, gave 30.9 g (95% of theory) of 5-amino-6-nitro-1,3-benzodioxole of melting point 203°-204° C.

Workup

  1. customequipped with a reflux condenser
  2. temperatureunder reflux for exactly 15 minutes
  3. customThe methanol was removed by distillation
  4. customthe last traces thereof, together with the glacial acetic acid, were removed by a two-fold evaporation with toluene
  5. filtrationcould be freed from the organic residues by suction filtration
  6. filtrationThe methylene chloride solution was filtered through silicon dioxide
  7. customevaporated in vacuo
  8. customThe residue, recrystallized from isopropanol

Sources & evidence

ORD record
ord-1497def4a61645ea8523405caf44c7d2
Source dataset
uspto-grants-1985_11
Patent number
US04554280

Reaction notes

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