Acetic Acid → HCID 13343750, compound

HRID 745577Notes

Reaction equation

HRID 745577 reaction equation
[CH3:1][CH:2]1[O:6][C:5]2[CH:7]=[C:8]([N+:15]([O-:17])=[O:16])[C:9]([NH:11]C(C)=O)=[CH:10][C:4]=2[O:3]1.C[O-].[Na+].C(O)(=O)C>CO>[CH3:1][CH:2]1[O:6][C:5]2[CH:7]=[C:8]([N+:15]([O-:17])=[O:16])[C:9]([NH2:11])=[CH:10][C:4]=2[O:3]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 13343745HCID 13343745, compound

Product 1

HCID 13343750HCID 13343750, compoundYield 90.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

39.6 g of 2-methyl-5-acetamino-6-nitro-1,3-benzodioxole were boiled at reflux for 1 hour in 4 l of methanol with 4 g of sodium methoxide. After adding 5 ml of glacial acetic acid, the solution was evaporated in vacuo. The last traces of glacial acetic acid were removed by evaporation with toluene. The residue was dissolved in methylene chloride and filtered through a small amount of silicon dioxide. The evaporated filtrate was crystallized from isopropanol. There were obtained 29.3 g (90.1% of theory) of 2-methyl-5-amino-6-nitro-1,3-benzodioxole of melting point 139° C.

Workup

  1. customthe solution was evaporated in vacuo
  2. customThe last traces of glacial acetic acid were removed by evaporation with toluene
  3. dissolutionThe residue was dissolved in methylene chloride
  4. filtrationfiltered through a small amount of silicon dioxide
  5. customThe evaporated filtrate was crystallized from isopropanol

Sources & evidence

ORD record
ord-4da35ccb65db4d91aa81727ed63db80c
Source dataset
uspto-grants-1986_07
Patent number
US04599347

Reaction notes

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